反应 #80587

反应方程式

HBr

1-(4-chlorophenoxy)-2-chloro-2-propene

N-bromosuccinimide

acetonitrile water

→

1-bromo-3-[(4-chlorophenoxy)phenyl]-2-propanone

收率 54.0%

溶剂

ether

反应条件

后处理

1. 1
   洗涤washed with 5% w/v of sodium thiosulfate
2. 2
   其他The organic layer was separated
3. 3
   洗涤washed with saturated sodium bicarbonate and brine
4. 4
   其他After drying
5. 5
   过滤(MgSO4), filtration and concentration in vacuo
6. 6
   其他the crude liquid (4.8 g) was chromatographed (silica gel, hexane/ethyl acetate, 80/20)

实验过程

To a turbid solution of 1-(4-chlorophenoxy)-2-chloro-2-propene from Step 1 (3 g, 15.7 mmol) in acetonitrile/water (4/1, 100 mL), N-bromosuccinimide (4.84 g, 31.4 mmol) was added in one lot. A catalytic amount of 48% HBr (40 μl) was added to the reaction and the yellowish orange mixture was stirred at room temperature. After 24 hours, the reaction mixture was diluted with ether and washed with 5% w/v of sodium thiosulfate. The organic layer was separated and washed with saturated sodium bicarbonate and brine. After drying (MgSO4), filtration and concentration in vacuo, the crude liquid (4.8 g) was chromatographed (silica gel, hexane/ethyl acetate, 80/20) to give crude 1-bromo-3-[(4-chlorophenoxy)phenyl]-2-propanone (2.3 g, 54%) which was used in the next step without further purification.

来源