反应 #988352

反应方程式

benzoic acid 2-fluoro-5-methyl-phenyl ester

N-bromo-succinimide

dibenzoy lperoxide

water

→

Benzoic acid 5-bromomethyl-2-fluoro-phenyl ester

溶剂

carbon tetrachloride

diethyl ether

反应条件

后处理

1. 1
   温度was heated
2. 2
   温度to reflux for 2 h (TLC monitored)
3. 3
   其他The organic layer was separated
4. 4
   洗涤washed with brine (20 mL)
5. 5
   干燥dried over sodium sulphate
6. 6
   浓缩concentrated under reduced pressure
7. 7
   其他The residue was purified by column chromatography (EtOAc:hexane, 1:25, Rf: 0.28)

实验过程

A mixture of benzoic acid 2-fluoro-5-methyl-phenyl ester (CAB02145, 2.47 g, 10.0 mmol), N-bromo-succinimide (1.96 g, 11.0 mmol) and dibenzoy lperoxide (10 mg) in carbon tetrachloride (25 mL) was heated to reflux for 2 h (TLC monitored). After cooling to room temperature, water (50 mL) and diethyl ether (100 mL) were added. The organic layer was separated, washed with brine (20 mL), dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography (EtOAc:hexane, 1:25, Rf: 0.28). Yield: 1.80 g (58%), white solid. 1H-NMR (400 MHz, CDCl3) δ=4.48 (s, 2H, —CH2Br), 7.18 (dd, J=9.8, 8.6 Hz, 1H), 7.28 (ddd, J=8.6, 4.3, 2.3 Hz, 1H), 7.34 (dd, J=7.0, 2.3 Hz, 1H), 7.50-7.55 (m, 2H), 7.64-7.69 (m, 1H), 8.18-8.23 (m, 2H). LRMS (FAB+): 229.1 (95), 309.0 (100, [M+H]+). Found: C, 54.1; H, 3.22%; C14H10BrFO2 (309.13) requires C, 54.39; H, 3.26%.

来源