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

HRID 1396575ノート

反応式

HRID 1396575 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7826c9ee850c496f931d0aba92e76347
出典データセット
uspto-grants-2014_12
特許番号
US08901134B2

反応ノート

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