Reference of 394-35-4,Some common heterocyclic compound, 394-35-4, name is Methyl 2-fluorobenzoate, molecular formula is C8H7FO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
5-amino-4-methylpyrimidine (5g, 45 mmol) was dissolved in 200 mL THF and cooled to -20°C. A solution of n-BuLi (112.5 mmol) was added over 10 minutes and the solution was kept at -20°C for 30 min, then warmed to room temp and stirred for 3h. It was then cooled to -40°C and to it was added methyl-2-fluorobenzoate (1.75 mL, 13.7 mmol) and the solution stirred at -40°C for 30 min and then warmed to room temp for lh. 50 mL of methanol was then added over 5 min, followed by 6N aq HC1. The solution was stirred for 18h at room temp. It was then neutralized with NaHC03 to pH 8 and then diluted with ethyl acetate and water. The organics were washed with water three times and then brine and dried over sodium sulfate and concentrated in vacuo.The crude material was purified by flash chromatography using 10percent methanol/ DCM. 1.5 g of product was isolated as a yellow solid (16percent). 1H-NMR: (<3/4-DMSO, 400 MHz) delta 12.22 (s, 1H), 8.86 (s, 1H), 8.83 (s, 1H), 7.98(dt, 1H), 7.46 (m, 1H), 7.38 (m, 2H), 7.02(s, 1H) LC/MS: calculated for Ci2H8FN3: 213.2; found 214.10 (M+H)+.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-fluorobenzoate, its application will become more common.
Reference:
Patent; GILEAD SCIENCES, INC.; BJORNSON, Kyla; BONDY, Steven, S.; CHOI, You-chul; CHOU, Chien-hung; MISHRA, Ruchika; TRENKLE, James, D.; TSE, Winston, C.; VIVIAN, Randall, W.; WO2011/146817; (2011); A1;,
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