Benzyl Bromide → Benzaldehyde, 5-bromo-3-fluoro-2-(phenylmethoxy)-

HRID 1396575노트

반응식

HRID 1396575 반응식
[Br:1][C:2]1[CH:3]=[C:4]([F:11])[C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[CH2:12]([O:10][C:5]1[C:4]([F:11])=[CH:3][C:2]([Br:1])=[CH:9][C:6]=1[CH:7]=[O:8])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

6

반응물 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 27792765-Bromo-3-fluoro-2-hydroxybenzaldehyde

생성물 1

HCID 86630410Benzaldehyde, 5-bromo-3-fluoro-2-(phenylmethoxy)-

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 5-Bromo-3-fluoro-2-hydroxy-benzaldehyde (5 g, 22.8 mmol) in DMF (100 ml) is added benzyl bromide (5.7 ml, 48 mmol) and cesium carbonate (11.9 g, 37 mmol). The reaction mixture is stirred at room temperature for 20 hours then diluted with water (150 ml) and extracted with EtOAc (2×150 ml), the organic portions are combined, washed with brine (50 ml), dried over MgSO4 and concentrated in vacuo to give a waxy off-white solid. The solid is stirred in iso-hexanes (30 ml) for 30 minutes, filtered and dried under vacuum to afford the title compound.

후처리

  1. extractionextracted with EtOAc (2×150 ml)
  2. washwashed with brine (50 ml)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customto give a waxy off-white solid
  6. filtrationfiltered
  7. customdried under vacuum

출처 및 근거

ORD 기록
ord-7826c9ee850c496f931d0aba92e76347
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901134B2

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