تفاعل #80587

معادلة التفاعل

HBr

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

N-bromosuccinimide

acetonitrile water

→

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

المردود 54.0%

المذيبات

ether

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر