Synthesis method of 3-phenoxy-2-aryl benzofuran compound

Abstract

The invention belongs to the field of organic synthesis, and particularly relates to a synthesis method of a 3-phenoxy-2-aryl benzofuran compound. In a nitrogen atmosphere, 1-fluoro-2-(phenoxymethyl) benzene compounds as shown in formulas 1 and 4, N-methyl-N-methyl benzamide compounds as shown in formulas 2 and 5 and tetrahydrofuran are mixed and heated in the presence of bis (trimethylsilyl) caesium to synthesize the 3-phenoxy-2-aryl benzofuran compounds as shown in formulas 3 and 6. The synthesis method disclosed by the invention is simple, economical, wider in applicability and suitable for large-scale production, and has very important influence on synthesis of furan compounds.

Description

Technical Field

[0001] This invention belongs to the field of organic synthesis, and specifically relates to a method for synthesizing 3-phenoxy-2-arylbenzofuran compounds. Background Technology

[0002] Benzofurans are widely used in the pharmaceutical field due to their broad bioactivity. They are also substrates for many reactions in organic synthesis. Despite extensive research on their synthesis, challenges remain, including the need for harsh or hazardous reaction conditions and the use of expensive or unstable reagents. Their unique bioactivity has attracted widespread attention from organic chemists. Conventional methods for synthesizing benzofurans typically include the Perkin rearrangement, Madelung cyclization, and condensation cyclization of phenols with α-halocarbonyl compounds. However, these methods usually involve harsh reaction conditions, require heavy metal catalysts, and have a relatively limited substrate range. Therefore, developing novel and efficient synthetic methods for benzofurans is of great significance and value. Summary of the Invention

[0003] This invention provides a one-pot synthesis method for benzofuran compounds under transition metal-free conditions. A series of 3-phenoxy-2-arylbenzofuran compounds were synthesized. This synthetic method achieves selective deprotonation at the benzylic position using rarely used CsN(SiMe3)2, providing an efficient, direct, mild, and simple method. The specific scheme is as follows:

[0004]

[0005] A method for synthesizing 3-phenoxy-2-arylbenzofuran compounds involves heating a mixture of 1-fluoro-2-(phenoxymethyl)benzene compounds (represented by formulas 1 and 4) and N-methyl-N-methylbenzamide compounds (represented by formulas 2 and 5), along with a strong base and an organic solvent, under a nitrogen atmosphere to synthesize 3-phenoxy-2-arylbenzofuran compounds (represented by formulas 3 and 6).

[0006] Where R 1 Selected from any one of phenoxy, 4-methylphenoxy, 4-fluorophenoxy, 4-tert-butylphenoxy, and 4-1,1'-biphenoxy; R 2 It is selected from any one of 3-methylphenyl, 4-methoxyphenyl, 4-tert-butylphenyl, 4-N,N-dimethylaminophenyl, and 4-methylthiophenyl.

[0007] The method of this invention achieves efficient synthesis of 3-phenoxy-2-arylbenzofuran compounds using alkali metals; the raw materials used in the synthesis method are inexpensive and readily available; R in this invention 1 R 2 It offers a variety of options and has wider applicability.

[0008] Preferably, the reaction is carried out in a nitrogen atmosphere.

[0009] Preferably, the synthesis takes place in the presence of a strong base and an organic solvent.

[0010] Preferably, the strong base is bis(trimethylsilylamino)cesium.

[0011] Preferably, the organic solvent is tetrahydrofuran.

[0012] Preferably, the reaction temperature is 110°C.

[0013] Preferably, the method of the present invention can synthesize 3-phenoxy-2-arylbenzofuran compounds with the following structures:

[0014]

[0015]

[0016] 3-phenoxy-2-arylbenzofuran compounds were synthesized by reacting 1-fluoro-2-(phenoxymethyl)benzene compounds and N-methyl-N-methoxybenzamide compounds with the organic solvent tetrahydrofuran in the presence of an equivalent amount of bis(trimethylsilylamino)cesium.

[0017] The technical solution of the present invention can achieve at least one of the following beneficial effects:

[0018] The raw materials 1 and 4 used in the synthesis method of the present invention are easy to prepare, and raw materials 2 and 5 are inexpensive and readily available;

[0019] The operation steps required by this invention are relatively simple, requiring no extreme heating or cooling, and the reaction can be carried out under normal pressure, making it safe and convenient.

[0020] R in this invention 1 R 2 The substrates available can be varied, thus the present invention has a wider range of applicability and can be used to synthesize various 3-phenoxy-2-arylbenzofuran compounds;

[0021] Compared with traditional methods, the method of this invention has many advantages such as high yield, mild conditions, and simple operation. Attached Figure Description

[0022] The attached figures show the proton and carbon NMR spectra of the products from each embodiment. The figure numbers correspond to the embodiment numbers. Figure A is the proton NMR spectrum, and Figure B is the carbon NMR spectrum. Figure 1A The above is the proton NMR spectrum of the product obtained in Example 1. Figure 1BThe carbon NMR spectrum of the product obtained in Example 1; Figure 2A The above is the proton NMR spectrum of the product obtained in Example 2. Figure 2B The carbon NMR spectrum of the product obtained in Example 2; Figure 3A The image shows the proton NMR spectrum of the product obtained in Example 3. Figure 3B The carbon NMR spectrum of the product obtained in Example 3; Figure 4A The above is the proton NMR spectrum of the product obtained in Example 4. Figure 4B The carbon NMR spectrum of the product obtained in Example 4; Figure 5A The above is the proton NMR spectrum of the product obtained in Example 5. Figure 5B The carbon NMR spectrum of the product obtained in Example 5; Figure 6A The above is the proton NMR spectrum of the product obtained in Example 6. Figure 6B The carbon NMR spectrum of the product obtained in Example 6; Figure 7A The above is the proton NMR spectrum of the product obtained in Example 7. Figure 7B The carbon NMR spectrum of the product obtained in Example 7; Figure 8A The above is the proton NMR spectrum of the product obtained in Example 8. Figure 8B The carbon NMR spectrum of the product obtained in Example 8; Figure 9A The image shows the proton NMR spectrum of the product obtained in Example 9. Figure 9B The carbon NMR spectrum of the product obtained in Example 9; Figure 10A The above is the proton NMR spectrum of the product obtained in Example 10. Figure 10B The image shows the carbon NMR spectrum of the product obtained in Example 10. Specific Implementation

[0023] To facilitate understanding by those skilled in the art, the concept of the present invention will be further explained below with reference to embodiments. The specific descriptions of the following embodiments are not intended to limit the present invention, but are merely for the convenience of those skilled in the art to understand the technical solution. All raw materials mentioned in the specification were purchased from the market or synthesized through simple methods. Other pharmaceuticals were purchased from Amex, Bide, Sigma-Aldrich, Acros, Alfa Aesar, Adamas-beta, or J&K. The nuclear magnetic resonance spectrometer was a Bruker 400M.

[0024] Example 1

[0025] Under a nitrogen atmosphere in a glove box, CsN(SiMe3)2 (58.6 mg, 2.0 equivalent) was loaded into a dry microwave tube (10 mL) with a magnetic inductor. Next, 0.5 mL of tetrahydrofuran (THF) was added to the microwave tube using a syringe. Then, 1-fluoro-2-(phenoxymethyl)benzene (60.6 mg, 0.3 mmol, 3.0 equivalent) and N-methyl-N-methoxybenzamide (16.5 mg, 0.1 mmol, 1.0 equivalent) were added to the reaction flask. The microwave tube was sealed with the cap and removed from the glove box. The reaction mixture was stirred in an oil bath at 110 °C for 12 hours. After the reaction was complete, the microwave tube was opened and exposed to air, and then three drops of water were slowly added to quench the reaction. The reaction mixture was passed through a silica short pad and washed with an additional 3 mL of ethyl acetate (3 × 1 mL), and the combined solutions were concentrated under reduced pressure. The crude product was purified by rapid silica gel column chromatography (eluting with petroleum ether) to obtain a white solid (28.6 mg, 88% yield). 1 H NMR (400MHz, CDCl3) δ: 8.08-7.96 (m, 2H), 7.53 (d, J=8.3Hz, 1H), 7.48-7.38 (m, 2H), 7.36-7.27 (m, 4H), 7.21-7.04 (m, 5H)ppm. 13 C{ 1 H} NMR (101MHz, CDCl3) δ: 157.1, 152.6, 143.8, 134.0, 129.9, 129.5, 128.9, 128.3, 125.2, 125.1, 123.8, 123.0, 122.9, 119.4, 116.2, 111.9ppm.

[0026] By changing the raw materials in Example 1, the following 10 sets of experimental examples were designed, where the first set of experiments is Example 1, and the corresponding NMR spectrum of the product is shown in Figure 1. The NMR spectra of the products in the remaining sets 2-10 correspond to the sequence numbers of the respective examples.

[0027] The table lists the structural formulas of the products in each of the 1-10 embodiments. The last column lists the yield of the products in each embodiment and indicates the specific implementation conditions of each embodiment. The specific meaning of the implementation conditions of each embodiment is shown below the table.

[0028]

[0029] Example 2

[0030] Under a nitrogen atmosphere in a glove box, CsN(SiMe3)2 (58.6 mg, 2.0 equivalent) was loaded into a dry microwave tube (10 mL) with a magnetic inductor. Next, 0.5 mL of tetrahydrofuran (THF) was added to the microwave tube using a syringe. Then, 1-fluoro-2-((4-methylphenoxy)methyl)benzene (64.8 mg, 0.3 mmol, 3.0 equivalent) and N-methyl-N-methoxybenzamide (16.5 mg, 0.1 mmol, 1.0 equivalent) were added to the reaction flask. The microwave tube was sealed with the cap and removed from the glove box. The reaction mixture was stirred in an oil bath at 110 °C for 12 hours. After the reaction was complete, the microwave tube was opened and exposed to air, and then three drops of water were slowly added to quench the reaction. The reaction mixture was passed through a silica short pad and washed with an additional 3 mL of ethyl acetate (3 × 1 mL), and the combined solutions were concentrated under reduced pressure. The crude product was purified by rapid silica gel column chromatography (eluting with petroleum ether) to obtain a white solid (21.6 mg, 72% yield). 1 H NMR (400MHz, CDCl3) δ: 8.05-8.00 (m, 2H), 7.53 (d, J=8.3Hz, 1H), 7.46-7.40 (m, 2H), 7.34-7.28(m, 2H), 7.20-7.10(m, 4H), 7.05-6.99(m, 2H), 2.33(s, 3H)ppm. 13 C{ 1 H}NMR (101MHz, CDCl3) δ: 155.0, 152.5, 143.7, 134.2, 132.4, 130.3, 129.6 , 128.8, 128.2, 125.1, 125.0, 123.9, 122.8, 119.4, 116.0, 111.9, 20.7ppm.

[0031] Example 3

[0032] Under a nitrogen atmosphere in a glove box, CsN(SiMe3)2 (58.6 mg, 2.0 equivalent) was loaded into a dry microwave tube (10 mL) with a magnetic inductor. Next, 0.5 mL of tetrahydrofuran (THF) was added to the microwave tube using a syringe. Then, 1-fluoro-2-((4-fluorophenoxy)methyl)benzene (66.1 mg, 0.3 mmol, 3.0 equivalent) and N-methyl-N-methoxybenzamide (16.5 mg, 0.1 mmol, 1.0 equivalent) were added to the reaction flask. The microwave tube was sealed with the cap and removed from the glove box. The reaction mixture was stirred in an oil bath at 110 °C for 12 hours. After the reaction was complete, the microwave tube was opened and exposed to air, and then three drops of water were slowly added to quench the reaction. The reaction mixture was passed through a silica short pad and washed with an additional 3 mL of ethyl acetate (3 × 1 mL), and the combined solutions were concentrated under reduced pressure. The crude product was purified by rapid silica gel column chromatography (eluting with petroleum ether) to obtain a white solid (22.8 mg, 75% yield). 1 H NMR (400MHz, CDCl3) δ: 8.03-7.97 (m, 2H), 7.55-7.50 (m, 1H), 7.46-7.40 (m, 2H), 7.35-7.28 (m, 2H), 7.15 (d, J=4.2Hz, 2H), 7.08-6.97 (m, 4H)ppm. 13 C{ 1 H}NMR (101MHz, CDCl3) δ: 159.8, 157.4, 153.1, 153.1, 152.6, 143.8, 134.2, 129.4, 128 .9, 128.4, 125.2, 125.2, 123.5, 123.0, 119.2, 117.4, 117.3, 116.5, 116.2, 112.0ppm.

[0033] Example 4

[0034] Under a nitrogen atmosphere in a glove box, CsN(SiMe3)2 (58.6 mg, 2.0 equivalent) was loaded into a dry microwave tube (10 mL) with a magnetic inductor. Next, 0.5 mL of tetrahydrofuran (THF) was drawn up with a syringe and added to the microwave tube. Then, 4-((2-fluorobenzyl)oxy)-1,1′-biphenyl (83.4 mg, 0.3 mmol, 3.0 equivalent) and N-methyl-N-methoxybenzamide (16.5 mg, 0.1 mmol, 1.0 equivalent) were added to the reaction flask. The microwave tube was sealed with the cap and removed from the glove box. The reaction mixture was stirred in an oil bath at 110 °C for 12 hours. After the reaction was complete, the microwave tube was opened and exposed to air, and then three drops of water were slowly added to quench the reaction. The reaction mixture was passed through a silica short pad and washed with another 3 mL of ethyl acetate (3 × 1 mL), and the combined solutions were concentrated under reduced pressure. The crude product was purified by rapid silica gel column chromatography (eluting with petroleum ether) to obtain a white solid (25.3 mg, 70% yield). 1 H NMR (400MHz, CDCl3) δ: 8.05-8.00 (m, 2H), 7.60-7.50 (m, 5H), 7.49-7.37 (m, 4H), 7.35-7.30 (m, 3H), 7.25-7.22 (m, 1H), 7.20-7.14 (m, 3H)ppm. 13 C{ 1 H}NMR (101MHz, CDCl3) δ: 156.7, 152.6, 143.9, 140.6, 136.1, 133.9, 129.5, 128.9, 128.5, 128.4, 127.1, 127.0, 125.2, 125.2, 123.8, 123.0, 119.4, 116.5, 112.0ppm.

[0035] Example 5

[0036] Under a nitrogen atmosphere in a glove box, CsN(SiMe3)2 (58.6 mg, 2.0 equivalent) was loaded into a dry microwave tube (10 mL) with a magnetic inductor. Next, 0.5 mL of tetrahydrofuran (THF) was added to the microwave tube using a syringe. Then, 1-((4-(tert-butyl)phenoxy)methyl)-2-fluorobenzene (77.4 mg, 0.3 mmol, 3.0 equivalent) and N-methyl-N-methoxybenzamide (16.5 mg, 0.1 mmol, 1.0 equivalent) were added to the reaction flask. The microwave tube was sealed with the cap and removed from the glove box. The reaction mixture was stirred in an oil bath at 110 °C for 12 hours. After the reaction was complete, the microwave tube was opened and exposed to air, and then three drops of water were slowly added to quench the reaction. The reaction mixture was passed through a silica short pad and washed with an additional 3 mL of ethyl acetate (3 × 1 mL), and the combined solutions were concentrated under reduced pressure. The crude product was purified by rapid silica gel column chromatography (eluting with petroleum ether) to obtain a white solid (27.0 mg, 79% yield). 1 H NMR (400MHz, CDCl3) δ: 8.07-8.00 (m, 2H), 7.54 (d, J = 8.3Hz, 1H), 7.44 (t, J = 7.7Hz, 2H), 7. 35-7.29(m, 4H), 7.26-7.18(m, 1H), 7.20-7.10(m, 1H), 7.08-7.03(m, 2H), 1.33(s, 9H)ppm. 13 C{ 1 H}NMR (101MHz, CDCl3) δ: 154.9, 152.6, 145.7, 143.8, 134.3, 129.6, 128.9, 12 8.2, 126.6, 125.2, 125.1, 124.0, 122.9, 119.5, 115.6, 111.9, 34.4, 31.6ppm.

[0037] Example 6

[0038] Under a nitrogen atmosphere in a glove box, CsN(SiMe3)2 (58.6 mg, 2.0 equivalent) was loaded into a dry microwave tube (10 mL) with a magnetic inductor. Next, 0.5 mL of tetrahydrofuran (THF) was added to the microwave tube using a syringe. Then, 1-fluoro-2-(phenoxymethyl)benzene (60.6 mg, 0.3 mmol, 3.0 equivalent) and N-methoxy-N,3-dimethylbenzamide (17.9 mg, 0.1 mmol, 1.0 equivalent) were added to the reaction flask. The microwave tube was sealed with the cap and removed from the glove box. The reaction mixture was stirred in an oil bath at 110 °C for 12 hours. After the reaction was complete, the microwave tube was opened and exposed to air, and then three drops of water were slowly added to quench the reaction. The reaction mixture was passed through a silica short pad and washed with an additional 3 mL of ethyl acetate (3 × 1 mL), and the combined solutions were concentrated under reduced pressure. The crude product was purified by rapid silica gel column chromatography (eluting with petroleum ether) to obtain a white solid (21.6 mg, 72% yield). 1 H NMR (400MHz, CDCl3) δ: 7.88-7.78 (m, 2H), 7.57-7.48 (m, 1H), 7.34-7.28 (m, 4H), 7.18-7.07 (m, 6H), 2.40 (s, 3H)ppm. 13 C{1H}NMR (101MHz, CDCl3) δ: 157.2, 152.5, 144.0, 138.5, 133.9, 129.8, 129.4, 129. 1, 128.8, 125.7, 125.0, 123.9, 122.9, 122.9, 122.5, 119.3, 116.3, 111.9, 21.7ppm.

[0039] Example 7

[0040] Under a nitrogen atmosphere in a glove box, CsN(SiMe3)2 (58.6 mg, 2.0 equivalent) was loaded into a dry microwave tube (10 mL) with a magnetic inductor. Next, 0.5 mL of tetrahydrofuran (THF) was added to the microwave tube using a syringe. Then, 1-fluoro-2-(phenoxymethyl)benzene (60.6 mg, 0.3 mmol, 3.0 equivalent) and N,4-dimethoxy-N-methylbenzamide (19.5 mg, 0.1 mmol, 1.0 equivalent) were added to the reaction flask. The microwave tube was sealed with the cap and removed from the glove box. The reaction mixture was stirred in an oil bath at 110 °C for 12 hours. After the reaction was complete, the microwave tube was opened and exposed to air, and then three drops of water were slowly added to quench the reaction. The reaction mixture was passed through a silica short pad and washed with an additional 3 mL of ethyl acetate (3 × 1 mL), and the combined solutions were concentrated under reduced pressure. The crude product was purified by rapid silica gel column chromatography (eluting with petroleum ether: ethyl acetate = 50:1) to give the product (24.0 mg, 76% yield) as a white solid. 1 H NMR (400MHz, CDCl3) δ: 7.97-7.92 (m, 2H), 7.51 (d, J=8.3Hz, 1H), 7.34-7.26 (m, 3H), 7.19-7.06 (m, 5H), 6.98-6.94 (m, 2H), 3.83 (s, 3H)ppm. 13 C{ 1 H}NMR (101MHz, CDCl3) δ: 159.7, 157.2, 152.3, 144.1, 132.4, 129.9, 126.8 , 124.6, 124.1, 122.9, 122.8, 122.3, 119.0, 116.1, 114.3, 111.7, 55.4ppm.

[0041] Example 8

[0042] Under a nitrogen atmosphere in a glove box, CsN(SiMe3)2 (58.6 mg, 2.0 equivalent) was loaded into a dry microwave tube (10 mL) with a magnetic inductor. Next, 0.5 mL of tetrahydrofuran (THF) was added to the microwave tube using a syringe. Then, 1-fluoro-2-(phenoxymethyl)benzene (60.6 mg, 0.3 mmol, 3.0 equivalent) and 4-tert-butyl-N-methoxy-N-methylbenzamide (22.1 mg, 0.1 mmol, 1.0 equivalent) were added to the reaction flask. The microwave tube was sealed with the cap and removed from the glove box. The reaction mixture was stirred in an oil bath at 110 °C for 12 hours. After the reaction was complete, the microwave tube was opened and exposed to air, and then three drops of water were slowly added to quench the reaction. The reaction mixture was passed through a silica short pad and washed with an additional 3 mL of ethyl acetate (3 × 1 mL), and the combined solutions were concentrated under reduced pressure. The crude product was purified by rapid silica gel column chromatography (eluting with petroleum ether) to obtain a white solid (28.4 mg, 83% yield). 1 H NMR (400MHz, CDCl3) δ: 7.95 (d, J=8.7Hz, 2H), 7.53 (dt, J=8.4, 0.8Hz, 1H), 7.49-7.44 (m, 2H), 7.34-7.27 (m, 3H), 7.20-7.06 (m, 5H), 1.34 (s, 9H)ppm. 13 C{ 1 H}NMR (101MHz, CDCl3) δ: 157.3, 152.5, 151.5, 144.2, 133.4, 129.8, 126.7, 12 5.8, 125.0, 124.9, 124.0, 122.9, 122.8, 119.2, 116.1, 111.9, 34.9, 31.3ppm.

[0043] Example 9

[0044] Under a nitrogen atmosphere in a glove box, CsN(SiMe3)2 (58.6 mg, 2.0 equivalent) was loaded into a dry microwave tube (10 mL) with a magnetic inductor. Next, 0.5 mL of tetrahydrofuran (THF) was added to the microwave tube using a syringe. Then, 1-fluoro-2-(phenoxymethyl)benzene (60.6 mg, 0.3 mmol, 3.0 equivalent) and N-methoxy-N-methyl-4-(methylthio)benzamide (21.1 mg, 0.1 mmol, 1.0 equivalent) were added to the reaction flask. The microwave tube was sealed with the cap and removed from the glove box. The reaction mixture was stirred in an oil bath at 110 °C for 12 hours. After the reaction was complete, the microwave tube was opened and exposed to air, and then three drops of water were slowly added to quench the reaction. The reaction mixture was passed through a silica short pad and washed with an additional 3 mL of ethyl acetate (3 × 1 mL), and the combined solutions were concentrated under reduced pressure. The crude product was purified by rapid silica gel column chromatography (eluting with petroleum ether: ethyl acetate = 50:1) to obtain the product (26.6 mg, 80% yield) as a white solid. 1 H NMR (400MHz, CDCl3) δ: 7.90 (d, J=8.6Hz, 2H), 7.50 (d, J=8.3Hz, 1H), 7.34-7.25 (m, 5H), 7.17-7.05 (m, 5H), 2.49 (s, 3H)ppm. 13 C{ 1 H} NMR (101MHz, CDCl3) δ: 157.1, 152.5, 143.6, 139.0, 133.6, 129.9, 126.4, 126.2, 125.5, 125.0, 123.8, 122.9, 119.2, 116.1, 111.8.15.6ppm.

[0045] Example 10

[0046] Under a nitrogen atmosphere in a glove box, CsN(SiMe3)2 (58.6 mg, 2.0 equivalent) was loaded into a dry microwave tube (10 mL) with a magnetic inductor. Next, 0.5 mL of tetrahydrofuran (THF) was drawn up with a syringe and added to the microwave tube. Then, 1-fluoro-2-(phenoxymethyl)benzene (60.6 mg, 0.3 mmol, 3.0 equivalent) and 4-(dimethylamino)-N-methoxy-N-methylbenzamide (20.8 mg, 0.1 mmol, 1.0 equivalent) were added to the reaction flask. The microwave tube was sealed with the cap and removed from the glove box. The reaction mixture was stirred in an oil bath at 110 °C for 12 hours. After the reaction was complete, the microwave tube was opened and exposed to air, and then three drops of water were slowly added to quench the reaction. The reaction mixture was passed through a silica short pad and washed with an additional 3 mL of ethyl acetate (3 × 1 mL), and the combined solutions were concentrated under reduced pressure. The crude product was purified by rapid silica gel column chromatography (eluting with petroleum ether: ethyl acetate = 50:1) to give the product (26.3 mg, 80% yield) as a white solid. 1 H NMR (400MHz, CDCl3) δ: 7.85 (d, J=9.0Hz, 2H), 7.47 (d, J=8.2Hz, 1H), 7.31-7.26 (m, 2H), 7.25-7.20(m, 1H), 7.16-7.02(m, 5H), 6.74(d, J=9.0Hz, 2H), 2.98(s, 6H)ppm. 1a C{ 1 H}NMR (101MHz, CDCl3) δ: 157.5, 152.1, 150.2, 145.2, 131.1, 129.8, 126.4 , 124.4, 123.9, 122.7, 122.5, 118.5, 117.5, 116.0, 112.2, 111.5, 40.4ppm.

Claims

1. A method for synthesizing a 3-phenoxy-2-arylbenzofuran compound, characterized in that: In a nitrogen atmosphere, 1-fluoro-2-(phenoxymethyl)benzene compounds shown in Formulas 1 and 4 and N-methyl-N-methylbenzamide compounds shown in Formulas 2 and 5 were mixed with tetrahydrofuran and heated in the presence of bistrimethylsilylaminocesium to synthesize 3-phenoxy-2-arylbenzofuran compounds shown in Formulas 3 and 6. Where R 1 Selected from any one of phenoxy, 4-methylphenoxy, 4-fluorophenoxy, 4-tert-butylphenoxy, and 4-1,1'-biphenoxy; R 2 It is selected from any one of 3-methylphenyl, 4-methoxyphenyl, 4-tert-butylphenyl, 4-N,N-dimethylaminophenyl, and 4-methylthiophenyl.

2. The synthesis method according to claim 1, characterized in that, The gas in question is nitrogen.

3. The synthesis method according to claim 1, characterized in that, The reaction temperature is 110℃.

4. The synthesis method according to claim 1, characterized in that, The 1-fluoro-2-(phenoxymethyl)benzene compounds, N-methyl-N-methylbenzamide compounds, and the product 3-phenoxy-2-arylbenzofuran compounds are listed in one of the following tables:

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