반응 #80587

반응 방정식

HBr

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

N-bromosuccinimide

acetonitrile water

→

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

수율 54.0%

용매

ether

반응 조건

후처리

1. 1
   세척washed with 5% w/v of sodium thiosulfate
2. 2
   기타The organic layer was separated
3. 3
   세척washed with saturated sodium bicarbonate and brine
4. 4
   기타After drying
5. 5
   여과(MgSO4), filtration and concentration in vacuo
6. 6
   기타the crude liquid (4.8 g) was chromatographed (silica gel, hexane/ethyl acetate, 80/20)

실험 절차

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.

출처