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

HRID 1461376

反応式

HRID 1461376 の反応式
[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

参加物

4

反応物 3

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

生成物 1

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

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-682d2dec772a4cda9c651257759b7e3b
出典データセット
uspto-grants-1991_12
特許番号
US05075319

関連ノート

読み込み中…