反应 #674373

反应方程式

tert-Butyl 4-bromo-2-chlorobenzoate

4-bromo-2-chlorobenzoic acid

di-tert-butyl dicarbonate

→

title compound

收率 51.0%

tert-Butyl 2-chloro-4-vinylbenzoate

收率 51.0%

溶剂

EtOAc

THF

反应条件

后处理

1. 1
   洗涤washed with water
2. 2
   洗涤The combined organic layer was washed with brine
3. 3
   干燥dried over Na2SO4
4. 4
   浓缩concentrated under reduced pressure
5. 5
   其他The residue was purified by flash chromatography (SiO2, 100-200 mesh; eluting with 2-3% EtOAc in n-hexane)

实验过程

tert-Butyl 4-bromo-2-chlorobenzoate (AI18). To a stirred solution of 4-bromo-2-chlorobenzoic acid (5 g, 21.37 mmol) in THF (30 mL) was added di-tert-butyl dicarbonate (25.5 g, 25.58 mmol), TEA (3.2 g, 31.98 mmol) and DMAP (0.78 g, 6.398 mmol), and the reaction mixture was stirred at 25° C. for 18 h. The reaction mixture was diluted with EtOAc and washed with water. The combined organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, 100-200 mesh; eluting with 2-3% EtOAc in n-hexane) to afford the title compound as a liquid (3.2 g, 51%): 1H NMR (400 MHz, CDCl3) δ 7.62 (m, 2H), 7.44 (d, J=8.4 Hz, 1H), 1.59 (s, 9H); ESIMS m/z 290.10 ([M+H]+); IR (thin film) 1728 cm−1.

来源