Hydrogen Bromide → 1-Bromo-3-[(4-chlorophenoxy)phenyl]-2-propanone

HRID 52309노트

반응식

HRID 52309 반응식
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8](Cl)=[CH2:9])=[CH:4][CH:3]=1.BrN1[C:18](=O)[CH2:17][CH2:16][C:15]1=O.[BrH:21].[C:22](#N)[CH3:23].[OH2:25]>CCOCC>[Br:21][CH2:22][C:23](=[O:25])[CH2:9][C:8]1[CH:15]=[CH:16][CH:17]=[CH:18][C:7]=1[O:6][C:5]1[CH:11]=[CH:12][C:2]([Cl:1])=[CH:3][CH:4]=1

참가 물질

6

반응물 4

HCID 260Hydrogen BromideHCID 67184N-bromobutanimideHCID 122548641-(4-Chlorophenoxy)-2-chloro-2-propeneHCID 18373917Acetonitrile--water (1/1)

생성물 1

HCID 229980221-Bromo-3-[(4-chlorophenoxy)phenyl]-2-propanone수율 54%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

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.

후처리

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

출처 및 근거

ORD 기록
ord-385fb46f10b44196a89d41e35fbede4c
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616601

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