Method for simultaneously preparing fluorophosgene and polysubstituted olefin compound

Abstract

The invention relates to the technical field of organic synthesis, in particular to a method for simultaneously preparing fluorophosgene and a polysubstituted olefin compound, which comprises the following steps: mixing difluorocyclobutyl ether and an organic solvent, stirring the mixed solution at a certain temperature to react, and then separating and purifying to obtain the fluorophosgene and the polysubstituted olefin compound. According to the synthesis method, the ring-opening reaction of the difluorocyclobutyl ether is realized, the fluorophosgene and the polysubstituted olefin compound are directly synthesized by a one-step method, the synthesis method is a new reaction mode, a simple and efficient method is provided for synthesizing the fluorophosgene and the polysubstituted olefin, the reaction conditions of the synthesis method are simple and efficient, additional catalysts and additives do not need to be added, and the synthesis method is suitable for industrial production. The related reaction conditions have good functional group tolerance and substrate universality, various functional groups such as ester groups, halogens and carbonyl can be compatible, and various straight-chain or branched-chain alkyl groups can also complete the reaction.

Description

Technical Field

[0001] The invention relates to the technical field of organic synthesis, and in particular to a method for simultaneously preparing fluorophosgene and multi-substituted olefin compounds. Background Art

[0002] Fluorophosgene is a very important organic synthesis intermediate with potential application value for acyl fluoridation, fluorination reaction and carbonylation reaction. However, there are still great challenges for its laboratory synthesis, such as the fact that the synthetic raw materials are not green enough, they are not easy to obtain and the produced fluorophosgene is difficult to use. For example, in 2020, the Riedel team used the very complex and rare [NEt3Me][ClF4] to react with CO gas to generate fluorophosgene. At this time, the fluorophosgene and the remaining CO gas are a mixture, and the remaining [NEt3Me][ClF2] cannot be reused (S. Riedel, Angew. Chem. Int. Ed. 2020, 59, 16002–16006). In the same year, the research group of Academician Chen Qingyun reported the generation of fluorophosgene from perfluoroalkyl ether carboxylic acid compounds in DMPU solvent under high temperature conditions, and also conducted related follow-up reaction research. This method is efficient and direct, but the cost is relatively expensive (Q.-Y. Chen, Org. Lett. 2020, 22, 8634-8637).

[0003] Polysubstituted conjugated olefins have special optoelectronic properties and play an indispensable role in the field of functional materials. As a special AIE (aggregation-induced emission) material, it has the advantages of high photoelectric efficiency and fast response. There are many methods for the synthesis of symmetrical polysubstituted olefins, while the synthesis of asymmetrical polysubstituted olefins is more difficult. Most of them require multi-step synthesis, and the selectivity is also difficult to control (Y. Yang, RSC Adv. 2021, 11, 20911–20915). Summary of the invention

[0004] The object of the present invention is to provide a method for simultaneously preparing fluorophosgene and polysubstituted olefin compounds, directly synthesizing fluorophosgene and polysubstituted olefin compounds in one step, which can be applied to the synthesis of fluorophosgene and polysubstituted olefins without the need for additional catalyst addition, with simple and efficient reaction conditions, good substrate universality and functional group tolerance.

[0005] The scheme adopted by the present invention to achieve the purpose is: a method for simultaneously preparing fluorophosgene and multi-substituted olefin compounds, wherein difluorocyclobutyl ether and an organic solvent are mixed, the mixed solution is stirred for reaction under certain temperature conditions, and then separated and purified to obtain the fluorophosgene and multi-substituted olefin compounds.

[0006] Preferably, the molecular structures of the fluorophosgene and the multi-substituted olefin compound are shown in Formulas I and II:

[0007]

[0008] The molecular structural formula of the difluorocyclobutyl ether is:

[0009] Wherein R1, R2, R3, and R4 are any one of an aryl group, an alkyl group, an alkoxy group, and a hydrogen atom, respectively, and may be the same or different. At most only one group among R1, R2, R3, and R4 is a hydrogen atom at the same time.

[0010] Preferably, the alkyl group has 1-20 carbon atoms and is a straight chain structure, a cyclic structure or a branched structure; the alkyl group carries one or more substituents. When there are multiple substituents, the substituents may be the same or different and the positions may be the same or different.

[0011] Preferably, the aryl group carries one or more substituents; when having multiple substituents, the substituents may be the same or different.

[0012] Preferably, the organic solvent is methanol, ethanol, isopropanol, tert-butyl alcohol, ether, dimethyl ether, methyl tert-butyl ether, 1,4-epoxyhexadecane, 1,3-epoxyhexadecane, dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, C 4-12 Saturated alkanes, C 3-12 Fluorinated or chlorinated alkanes, benzene, toluene, xylene, trimethylbenzene, dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, acetone, N-methylpyrrolidone, acetonitrile, C 3-12 At least one of the saturated alkyl nitriles.

[0013] Preferably, the concentration of the difluorobutyl ether is between 0.01M and 1M.

[0014] Preferably, the reaction temperature is 0-150°C.

[0015] Preferably, the separation and purification includes filtration, concentration, recrystallization and column chromatography.

[0016] The present invention has the following advantages and beneficial effects:

[0017] (1) The synthesis method of the present invention realizes the ring-opening reaction of difluorocyclobutyl ether and directly synthesizes fluorophosgene and polysubstituted olefin compounds in one step. It is a new reaction mode and provides a simple and efficient method for synthesizing fluorophosgene and polysubstituted olefins.

[0018] (2) The synthesis method of the present invention has simple reaction conditions, high efficiency, and does not require the addition of additional catalysts and additives.

[0019] (3) The reaction conditions involved in the synthesis method of the present invention have good functional group tolerance and substrate universality, and are compatible with various functional groups such as ester groups, halogen groups, and carbonyl groups. Various straight-chain or branched alkyl groups can also complete the reaction.

[0020] (4) The mixture of fluorophosgene and multi-substituted olefin compound prepared by the present invention is directly subjected to the next reaction without being separated separately. DETAILED DESCRIPTION

[0021] For a better understanding of the present invention, the following examples are provided to further illustrate the present invention, but the present invention is not limited to the following examples.

[0022] Embodiment 1:

[0023]

[0024] A (35.2 mg, 0.1 mmol, 1 equiv.) and dried MeCN (2 mL) were added to a dry photoreaction tube equipped with a magnetic stirrer and sealed. The reaction mixture was stirred at 110°C for 4 hours. The reaction mixture was concentrated under reduced pressure and fluorophosgene was used 19 The content of the soluble compound in acetonitrile was detected by F NMR. The crude product was purified by silica gel column chromatography (200-300 mesh) and eluted with PE / EA (100 / 1-50 / 1, v / v) to obtain the target compound G1 (colorless solid 24.6 mg, yield 86%). 19 The content of dissolved fluorophosgene in acetonitrile was 25% by F NMR.

[0025] 1 H NMR (600 MHz, CDCl 3, 25℃)δ7.37–7.33(m,3H),7.32–7.29(m,4H),7.28–7.25(m,1H),7.24–7.2 2(m,2H),6.98–6.95(m,2H),6.93(s,1H),6.69–6.67(m,2H),3.76(s,3H). 13 CNMR (151MHz, CDCl 3, 25℃)δ158.5,143.7,140.8,140.7,130.9,130.6,130.2,128.9,128.3,127.8,127.5,127.4,127 .3,113.5,55.3.IR(ATR):3056,2944,1602,1509,1421,1300,1252,1177,1036,827,734,701cm 1.HRMS(APCI,m / z):calcd for C 21 H 18 O + (M+H) + :286.1352; found:286.1351.

[0026] Embodiment 2:

[0027]

[0028] A (35.2 mg, 0.1 mmol, 1 equiv.) and dried toluene (2 mL) were added to a dry photoreaction tube equipped with a magnetic stirrer and sealed. The reaction mixture was stirred at 110°C for 4 hours. The reaction mixture was concentrated under reduced pressure and fluorophosgene was used 19 The content of the soluble substance in acetonitrile was detected by F NMR. The crude product was purified by silica gel column chromatography (200-300 mesh) and eluted with PE / EA (100 / 1-50 / 1, v / v) to obtain the target compound G1 (colorless solid 8.9 mg, yield 31%). 19 The content of dissolved fluorophosgene in acetonitrile was 5% by F NMR.

[0029] 1 H NMR (600 MHz, CDCl 3, 25℃)δ7.37–7.33(m,3H),7.32–7.29(m,4H),7.28–7.25(m,1H),7.24–7.2 2(m,2H),6.98–6.95(m,2H),6.93(s,1H),6.69–6.67(m,2H),3.76(s,3H). 13 CNMR (151MHz, CDCl 3, 25℃)δ158.5,143.7,140.8,140.7,130.9,130.6,130.2,128.9,128.3,127.8,127.5,127.4,127 .3,113.5,55.3.IR(ATR):3056,2944,1602,1509,1421,1300,1252,1177,1036,827,734,701cm 1 .HRMS(APCI,m / z):calcd for C 21 H 18 O + (M+H) + :286.1352; found:286.1351.

[0030] Embodiment 3:

[0031]

[0032] A (35.2 mg, 0.1 mmol, 1 equiv.) and dried DCE (2 mL) were added to a dry photoreaction tube equipped with a magnetic stirrer and sealed. The reaction mixture was stirred at 110°C for 4 hours. After cooling, the reaction mixture was concentrated under reduced pressure and fluorophosgene was used. 19 The crude product was purified by silica gel column chromatography (200-300 mesh) and eluted with PE / EA (100 / 1-50 / 1, v / v) to obtain the target compound G1 (colorless solid 16.1 mg, yield 56%). 19 The content of dissolved fluorophosgene in acetonitrile was 14% by F NMR.

[0033] 1 H NMR (600 MHz, CDCl 3, 25℃)δ7.37–7.33(m,3H),7.32–7.29(m,4H),7.28–7.25(m,1H),7.24–7.2 2(m,2H),6.98–6.95(m,2H),6.93(s,1H),6.69–6.67(m,2H),3.76(s,3H). 13 CNMR (151MHz, CDCl 3, 25℃)δ158.5,143.7,140.8,140.7,130.9,130.6,130.2,128.9,128.3,127.8,127.5,127.4,127 .3,113.5,55.3.IR(ATR):3056,2944,1602,1509,1421,1300,1252,1177,1036,827,734,701cm 1 .HRMS(APCI,m / z):calcd for C 21 H 18 O + (M+H) + :286.1352; found:286.1351.

[0034] Embodiment 4:

[0035]

[0036] A (35.2 mg, 0.1 mmol, 1 equiv.) and dried MeCN (5 mL) were added to a dry photoreaction tube equipped with a magnetic stirrer and sealed. The reaction mixture was stirred at 110°C for 4 hours. The reaction mixture was concentrated under reduced pressure and fluorophosgene was used 19 The crude product was purified by silica gel column chromatography (200-300 mesh) and eluted with PE / EA (100 / 1-50 / 1, v / v) to obtain the target compound G1 (colorless solid 23.2 mg, yield 81%). 19 The content of dissolved fluorophosgene in acetonitrile was 47% by F NMR.

[0037] 1 H NMR (600 MHz, CDCl 3, 25℃)δ7.37–7.33(m,3H),7.32–7.29(m,4H),7.28–7.25(m,1H),7.24–7.2 2(m,2H),6.98–6.95(m,2H),6.93(s,1H),6.69–6.67(m,2H),3.76(s,3H). 13 CNMR (151MHz, CDCl 3, 25℃)δ158.5,143.7,140.8,140.7,130.9,130.6,130.2,128.9,128.3,127.8,127.5,127.4,127 .3,113.5,55.3.IR(ATR):3056,2944,1602,1509,1421,1300,1252,1177,1036,827,734,701cm 1 .HRMS(APCI,m / z):calcd for C 21 H 18 O + (M+H) + :286.1352; found:286.1351.

[0038] Embodiment 5:

[0039]

[0040] A (35.2 mg, 0.1 mmol, 1 equiv.) and dried MeCN (0.5 mL) were added to a dry photoreaction tube equipped with a magnetic stirrer and sealed. The reaction mixture was stirred at 110°C for 4 hours. The reaction mixture was concentrated under reduced pressure and fluorophosgene was used 19The content of the soluble substance in acetonitrile was detected by F NMR. The crude product was purified by silica gel column chromatography (200-300 mesh) and eluted with PE / EA (100 / 1-50 / 1, v / v) to obtain the target compound G1 (colorless solid 25.2 mg, yield 87%). 19 The content of dissolved fluorophosgene in acetonitrile was 14% by F NMR.

[0041] 1 H NMR (600 MHz, CDCl 3, 25℃)δ7.37–7.33(m,3H),7.32–7.29(m,4H),7.28–7.25(m,1H),7.24–7.2 2(m,2H),6.98–6.95(m,2H),6.93(s,1H),6.69–6.67(m,2H),3.76(s,3H). 13 CNMR (151MHz, CDCl 3, 25℃)δ158.5,143.7,140.8,140.7,130.9,130.6,130.2,128.9,128.3,127.8,127.5,127.4,127 .3,113.5,55.3.IR(ATR):3056,2944,1602,1509,1421,1300,1252,1177,1036,827,734,701cm 1 .HRMS(APCI,m / z):calcd for C 21 H 18 O + (M+H) + :286.1352; found:286.1351.

[0042] Embodiment 6:

[0043]

[0044] A (35.2 mg, 0.1 mmol, 1 equiv.) and dried MeCN (0.5 mL) were added to a dry photoreaction tube equipped with a magnetic stirrer and sealed. The reaction mixture was stirred at 110°C for 4 hours. The reaction mixture was concentrated under reduced pressure and fluorophosgene was used 19 The content of the soluble compound in acetonitrile was detected by F NMR. The crude product was purified by silica gel column chromatography (200-300 mesh) and eluted with PE / EA (100 / 1-50 / 1, v / v) to obtain the target compound G1 (colorless solid 20.4 mg, yield 71%). 19 The content of dissolved fluorophosgene in acetonitrile was 23% by F NMR.

[0045] 1 H NMR (600 MHz, CDCl 3, 25℃)δ7.37–7.33(m,3H),7.32–7.29(m,4H),7.28–7.25(m,1H),7.24–7.2 2(m,2H),6.98–6.95(m,2H),6.93(s,1H),6.69–6.67(m,2H),3.76(s,3H). 13 CNMR (151MHz, CDCl 3, 25℃)δ158.5,143.7,140.8,140.7,130.9,130.6,130.2,128.9,128.3,127.8,127.5,127.4,127 .3,113.5,55.3.IR(ATR):3056,2944,1602,1509,1421,1300,1252,1177,1036,827,734,701cm 1 .HRMS(APCI,m / z):calcd for C 21 H 18 O + (M+H) + :286.1352; found:286.1351.

[0046] Embodiment 7:

[0047]

[0048] A (37.8 mg, 0.1 mmol, 1 equiv.) and dried MeCN (2 mL) were added to a dry photoreaction tube equipped with a magnetic stirrer and sealed. The reaction mixture was stirred at 110°C for 4 hours. The reaction mixture was concentrated under reduced pressure and fluorophosgene was used 19 The crude product was purified by silica gel column chromatography (200-300 mesh) and eluted with PE / EA (100 / 1-50 / 1, v / v) to obtain the target compound G1 (colorless solid 28.7 mg, yield 92%). 19 The content of dissolved fluorophosgene in acetonitrile was 31% by F NMR.

[0049] 1 H NMR (600 MHz, CDCl 3, 25℃) δ7.38–7.33(m,3H),7.32–7.27(m,4H),7.27–7.22(m,3H),7.16–7.14(m,2H),6.97–6.94(m,3H),1.25(s,9H). 13C NMR (151 MHz, CDCl 3, 25℃)δ150.0,143.7,141.7,140.8,134.5,130.4,129.4,128.9,128.3,128.1,127.6,127.5, 127.5,125.1,34.6,31.4.IR(ATR):3063,2955,1740,1494,1446,1362,1271,827,764,700cm 1 .HRMS(ESI,m / z):calcd for C 24 H 25 + (M+H) + :313.1951; found:313.1958.

[0050] Embodiment 8:

[0051]

[0052] A (40.6 mg, 0.1 mmol, 1 equiv.) and dried MeCN (2 mL) were added to a dry photoreaction tube equipped with a magnetic stirrer and sealed. The reaction mixture was stirred at 110°C for 4 hours. The reaction mixture was concentrated under reduced pressure and fluorophosgene was used 19 The content of the soluble substance in acetonitrile was detected by F NMR. The crude product was purified by silica gel column chromatography (200-300 mesh) and eluted with PE / EA (100 / 1-50 / 1, v / v) to obtain the target compound G1 (colorless solid 30.9 mg, yield 91%). 19 The content of dissolved fluorophosgene in acetonitrile was 31% by F NMR.

[0053] 1 H NMR (600 MHz, CDCl 3, 25℃)δ7.23–7.20(m,2H),7.18–7.15(m,4H),7.13–7.10(m,4H),7.00–6.97(m,2H),6.89(s,1H),2.41(s,3H),2.35(s,3H),1.27(s,9H). 13 C NMR (151 MHz, CDCl 3,25℃) δ149.7,141.6,141.2,137.9,137.2,137.0,134.8,130.3,129.5,129.3,129.0,127.5,127.1,125. 1,34.6,31.4,21.5,21.3.IR(ATR):2963,2922,1658,1569,1513,1364,1267,1110,1021,909,827,734cm 1 .HRMS(APCI,m / z):calcd for C 26 H 29 + (M+H) + :341.2264; found:341.2263.

[0054] Embodiment 9:

[0055]

[0056] A (40.0 mg, 0.1 mmol, 1 equiv.) and dried MeCN (2 mL) were added to a dry photoreaction tube equipped with a magnetic stirrer and sealed. The reaction mixture was stirred at 110°C for 4 hours. The reaction mixture was concentrated under reduced pressure and fluorophosgene was used 19 The content of the soluble substance in acetonitrile was detected by F NMR. The crude product was purified by silica gel column chromatography (200-300 mesh) and eluted with PE / EA (100 / 1-50 / 1, v / v) to obtain the target compound G1 (colorless solid 30.9 mg, yield 91%). 19 The content of dissolved fluorophosgene in acetonitrile was 31% by F NMR.

[0057] 1 H NMR (600 MHz, CDCl 3, 25℃)7.26-7.34(m,8H),7.23(d,2H,J=8.2Hz),7.15-7.19(m,2H),6.84-6.89(m,3H),. 13 C NMR (150 MHz, CDCl 3, 25℃)120.5,126.8,127.57,127.63,127.7,128.2,128.7,130.2,131.0,131.1,136.3,139 .9,143.0,143.4.IR(neat):3023,1489,1443,1072,1007,882,762cm-1.HRMS:Calcd.for C20H15Br:334.0357.Found:334.0339.

[0058] Embodiment 10:

[0059]

[0060] A (38.0 mg, 0.1 mmol, 1 equiv.) and dried MeCN (2 mL) were added to a dry photoreaction tube equipped with a magnetic stirrer and sealed. The reaction mixture was stirred at 110°C for 4 hours. The reaction mixture was concentrated under reduced pressure and fluorophosgene was used 19 The crude product was purified by silica gel column chromatography (200-300 mesh) and eluted with PE / EA (100 / 1-50 / 1, v / v) to obtain the target compound G1 (colorless solid 23.6 mg, yield 75%). 19 The content of dissolved fluorophosgene in acetonitrile was 20% by F NMR.

[0061] 1 H NMR (400 MHz, CDCl 3, 25℃) δ7.79(d,J=8.4Hz,2H),7.33(s,8H),7.21-7.14(m,2H),7.07(d,J=8.4Hz,2H),6.98(s,1H),3.86(s,3H). 13 C NMR (101 MHz, CDCl 3, 25℃)δ166.9,145.1,142.9,142.2,139.8,130.3,129.4,129.2,128.7,128.3,128.0,127.8,127.8,127.1,52.0.HRMS(ESI):m / z calculated for C22H18O2 + [M+H]+314.1301, found314.1304.

[0062] Embodiment 11:

[0063]

[0064] A (33.6 mg, 0.1 mmol, 1 equiv.) and dried MeCN (2 mL) were added to a dry photoreaction tube equipped with a magnetic stirrer and sealed. The reaction mixture was stirred at 110°C for 4 hours. The reaction mixture was concentrated under reduced pressure and fluorophosgene was used 19The crude product was purified by silica gel column chromatography (200-300 mesh) and eluted with PE / EA (100 / 1-50 / 1, v / v) to obtain the target compound G1 (colorless solid 21.6 mg, yield 80%). 19 The content of dissolved fluorophosgene in acetonitrile was 22% by F NMR.

[0065] 1 H NMR (400 MHz, CDCl 3, 25℃)δ7.37–7.31(m,2H),7.28–7.21(m,4H),7.17–7.11(m,4H),7.05–6.97(m,3H),6.93–6.86(m,2H),2.14(s,3H). 13 C NMR (101 MHz, CDCl 3, 25℃) δ144.2,143.7,143.2,139.5,135.9,131.0,130.1,129.4,128.3,128.0,127.6,126.7,126.3,126.0,23.5.

[0066] Embodiment 12:

[0067]

[0068] A (39.8 mg, 0.1 mmol, 1 equiv.) and dried MeCN (2 mL) were added to a dry photoreaction tube equipped with a magnetic stirrer and sealed. The reaction mixture was stirred at 110°C for 4 hours. The reaction mixture was concentrated under reduced pressure and fluorophosgene was used 19 The content of the soluble substance in acetonitrile was detected by F NMR. The crude product was purified by silica gel column chromatography (200-300 mesh) and eluted with PE / EA (100 / 1-50 / 1, v / v) to obtain the target compound G1 (colorless solid 25.9 mg, yield 78%). 19 The content of dissolved fluorophosgene in acetonitrile was 21% by F NMR.

[0069] 1 H NMR (400 MHz, CDCl 3, 25℃): δ7.11-7.09(m,12H),7.04-7.01(m,8H); 13 C NMR (101 MHz, CDCl 3,25℃): δ143.8,141.1,131.5,127.8,126.5ppm.HRMS(ESI)m / z:calcd forC26H21[M+H]+333.1638, found 333.1647.

[0070] React Extensions:

[0071]

[0072] A (39.8 mg, 0.1 mmol, 1 equiv.), benzyl alcohol (32.4 mg, 0.3 mmol, 3 equiv.) and dry MeCN (2 mL) were added to a dry photoreaction tube equipped with a magnetic stirrer and sealed. The reaction mixture was stirred at 110°C for 4 hours and then reacted at room temperature for 12 hours. The reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (200-300 mesh) and eluted with PE / EA (100 / 1-50 / 1, v / v) to obtain the target compound G1 (colorless solid 25.9 mg, yield 78%). Carbonate G8 (white solid 17.4 mg, 72%).

[0073] 1H NMR (300MHz, DMSO-d6) δ7.36–7.24 (m, 10H), 5.53 (s, 4H). HRMS (ESI): Calcd for C15H14O3 (M+H) + 242.09, found 242.10.

[0074] The above is only a preferred embodiment of the present invention, which certainly cannot be used to limit the scope of rights of the present invention. It should be pointed out that for ordinary technicians in this technical field, several improvements and changes can be made without departing from the principle of the present invention, and these improvements and changes are also regarded as the protection scope of the present invention.

Claims

1. A method for simultaneously preparing fluorophosgene and a multi-substituted olefin compound, characterized in that: The fluorophosgene and the multi-substituted olefin compound can be obtained by mixing difluorocyclobutyl ether and an organic solvent, stirring the mixed solution for reaction under certain temperature conditions, and then separating and purifying.

2. The method for simultaneously preparing fluorophosgene and a multi-substituted olefin compound according to claim 1, characterized in that: The molecular structural formulas Ⅰ and Ⅱ of the fluorophosgene and multi-substituted olefin compound are as shown in: The molecular structural formula of the difluorocyclobutyl ether is: Wherein R1, R2, R3, and R4 are any one of an aryl group, an alkyl group, an alkoxy group, and a hydrogen atom, respectively, and may be the same or different. At most only one group among R1, R2, R3, and R4 is a hydrogen atom at the same time.

3. The method for simultaneously preparing fluorophosgene and a multi-substituted olefin compound according to claim 2, characterized in that: The alkyl group has 1 to 20 carbon atoms and is a straight chain structure, a cyclic structure or a branched structure; the alkyl group carries one or more substituents. When there are multiple substituents, the substituents may be the same or different, and the positions may be the same or different.

4. The method for simultaneously preparing fluorophosgene and a multi-substituted olefin compound according to claim 2, characterized in that: The aryl group has one or more substituents; when having multiple substituents, the substituents may be the same or different.

5. The method for simultaneously preparing fluorophosgene and a multi-substituted olefin compound according to claim 1, characterized in that: The organic solvent is methanol, ethanol, isopropanol, tert-butyl alcohol, ether, dimethyl ether, methyl tert-butyl ether, 1,4-epoxyhexadecane, 1,3-epoxyhexadecane, dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, C 4-12 Saturated alkanes, C 3-12 Fluorinated or chlorinated alkanes, benzene, toluene, xylene, trimethylbenzene, dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, acetone, N-methylpyrrolidone, acetonitrile, C 3-12 At least one of the saturated alkyl nitriles.

6. The method for simultaneously preparing fluorophosgene and a multi-substituted olefin compound according to claim 1, characterized in that: The concentration of the difluorobutyl ether is between 0.01M and 1M.

7. The method for simultaneously preparing fluorophosgene and a multi-substituted olefin compound according to claim 1, characterized in that: The reaction temperature is 0-150°C.

8. The method for simultaneously preparing fluorophosgene and a multi-substituted olefin compound according to claim 1, characterized in that: The separation and purification includes filtration, concentration, recrystallization and column chromatography.

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