Potassium Carbonate → 1-(2',5',5-Trifluoro-1,1'-biphenyl-2-yl)ethanone

HRID 2181914노트

반응식

HRID 2181914 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].Br[C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[C:26](=[O:28])[CH3:27]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[C:26](=[O:28])[CH3:27]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 2734335(2,5-Difluorophenyl)boronic acidHCID 27363041-(2-Bromo-4-fluorophenyl)ethan-1-one

생성물 1

HCID 224822741-(2',5',5-Trifluoro-1,1'-biphenyl-2-yl)ethanone수율 27.2%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 167845palladium(II) acetate촉매

실험 절차

The title compound was prepared from 2,5-difluorophenylboronic acid (2.0 g, 12.7 mmol), tetrabutylammonium bromide (3.71 g, 11.5 mmol), potassium carbonate (4.78 g, 34.6 mmol), 2′-bromo-4′-fluoroacetophenone (2.5 g, 11.5 mmol), and palladium acetate (259 mg, 1.15 mmol) according to the procedure and in the same manner as described in Example 105, step a. The product was purified by preparative liquid chromatography on a Biotage® 40 Mi column of prepacked silica gel (90 g), eluting with a gradient of 10%-30% methyl tert-butyl ether in hexane, to afford the desired compound (784 mg, 27%) as a clear yellow oil.

후처리

  1. customThe product was purified by preparative liquid chromatography on a Biotage® 40 Mi column of prepacked silica gel (90 g)
  2. washeluting with a gradient of 10%-30% methyl tert-butyl ether in hexane

출처 및 근거

ORD 기록
ord-2d0eb55734bf4c42a36d138b27b01c32
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06894061B2

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