A kind of preparation method of m-aminophenylacetylene
A technology of aminophenylacetylene and m-aminobenzene is applied in the field of preparation of m-aminophenylacetylene, and can solve the problems of unsuitability for industrial production, complicated operation, high toxicity and the like
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[0073] The first aspect of the present invention provides a method for preparing m-aminophenylacetylene (compound of formula V), which may include: preparing a compound of formula III through a coupling reaction between a compound of formula I and a compound of formula II, and the reaction equation is as follows:
[0074]
[0075] Wherein, X is selected from Cl, Br, I, OMs (-O-SO 2 CH 3 ), OTf(-O-SO 2 CF 3 );
[0076] R 1 selected from H, -CH(CH 3 ) 2 OH(2-Hydroxy-isopropyl), -Si(CH 3 ) 3 ;
[0077] R 2 Selected from H, alkyl, aryl.
[0078] In the preparation method of m-aminophenylacetylene provided by the present invention, R 2 Can be H, alkyl, aryl, etc. The alkyl group can be a C1-C6 alkyl group, more specifically, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, etc., more specifically, for example, methyl, ethyl, n-propyl, Isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, cyclobutyl, etc.; the aryl can be substituted or unsubstit...
Embodiment 1
[0104]
[0105] Compound 2 (181g, 1mol), acetamide (71g, 1.2mol), potassium phosphate (297g, 1.4mol), palladium acetate (2.25g, 0.01mol), ligand compound t-BuBrettPhos (10.6g, 0.022mol ), 2ml of deionized water was added to 2L of tert-butanol, heated to 110°C under the protection of nitrogen, and refluxed for 4.5 hours. Ethyl ester was stirred, and the insoluble matter was filtered. The filtrate was washed with 2L of water, the water layer was separated, and the organic layer was evaporated to remove the solvent under reduced pressure to obtain the crude product of compound 3 as a white solid (148g), with a purity of 97.8% and a yield of 93%. for the next reaction. 1 H NMR (400MHz, CDCl3): δ2.13(s, 3H), 3.04(s, 1H), 7.20(d, J=6.8Hz, 2H), 7.48-7.49(m, 1H), 7.67(s, 1H ),8.60(s,1H);
[0106] Add compound 3 (148g, 0.93mol) to 280g of 20% aqueous sodium hydroxide solution, add 100ml of ethanol, heat to 70°C, stir for 2 hours, TLC shows that the reaction is complete, and cool t...
Embodiment 2
[0116]
[0117] Compound 4 (97.3g, 0.5mol), benzamide (72g, 0.6mol), potassium phosphate (148.6g, 0.7mol), palladium acetate (1.13g, 0.005mol), ligand compound Xantphos (6.36g, 0.011mol), 1ml of deionized water was added to 1L of tert-butanol, heated to 110°C under nitrogen protection, and refluxed for 6.5 hours. TLC showed that the reaction was complete. L ethyl acetate, stirred, filtered insoluble matter, the filtrate was washed with 1 L of water, the water layer was separated, the organic layer was evaporated to remove the solvent under reduced pressure, and the crude product of Compound 5 was obtained as an off-white solid (121.5g), with a purity of 98.1%, and a yield of 87.8 %, can be directly used in the next step reaction. 1H NMR (400MHz, CDCl3): δ3.08(s, 1H), 7.25-7.30(m, 2H), 7.43(t, J=7.2Hz, 2H), 7.52(t, J=7.2Hz, 1H), 7.66 (d, J = 7.2Hz, 1H), 7.76 (s, 1H), 7.83 (d, J = 7.6Hz, 2H), 1.47 (s, 6H).
[0118] Compound 5 (100.5g, 0.36mol) was added to 150g of 20% potas...
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