Diethyl Carbonate → Ethyl 4-bromo-2,5-difluoro-β-oxobenzenepropanoate

HRID 1461376노트

반응식

HRID 1461376 반응식
[CH3:1][C:2]([C:4]1[C:9]([F:10])=[CH:8][C:7]([Br:11])=[C:6]([F:12])[CH:5]=1)=[O:3].[C:13](=O)([O:17]CC)[O:14][CH2:15][CH3:16].[H-].[Na+]>>[Br:11][C:7]1[C:6]([F:12])=[CH:5][C:4]([C:2]([CH2:1][C:13]([O:14][CH2:15][CH3:16])=[O:17])=[O:3])=[C:9]([F:10])[CH:8]=1

참가 물질

4

반응물 3

HCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 99916531-(4-Bromo-2,5-difluorophenyl)ethan-1-one

생성물 1

HCID 10018069Ethyl 4-bromo-2,5-difluoro-β-oxobenzenepropanoate

반응 조건

온도
80 °C

실험 절차

To a stirred mixture of 18 g 4-bromo-2,5-difluoroacetophenone and 233 ml diethyl carbonate cooled in an ice-bath was slowly added 6.4 g sodium hydride (60% in oil). The reaction mixture was heated at 80° C. for 90 min. and then added to 700 ml ice containing 25 ml acetic acid. The aqueous mixture was extracted with ether, and the ether extracts were washed with sodium chloride solution, dried (magnesium sulfate) and concentrated. The residue was distilled, collecting the material (15.33 g) boiling at 85°-135° C. (0.05 mm). The latter material was chromatographed on 185 g silica gel (Kieselgel 60) using 20% ether in hexane as eluant to give 6.69 g ethyl 4-bromo-2,5-difluorobenzoylacetate as the first product to be eluted.

후처리

  1. temperaturecooled in an ice-bath
  2. extractionThe aqueous mixture was extracted with ether
  3. washthe ether extracts were washed with sodium chloride solution
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated
  6. distillationThe residue was distilled
  7. customcollecting the material (15.33 g) boiling at 85°-135° C. (0.05 mm)
  8. customThe latter material was chromatographed on 185 g silica gel (Kieselgel 60)

출처 및 근거

ORD 기록
ord-682d2dec772a4cda9c651257759b7e3b
출처 데이터셋
uspto-grants-1991_12
특허 번호
US05075319

반응 노트

불러오는 중…