Benzyl Bromide → 5-(Benzyloxy)-2-bromobenzaldehyde

HRID 1181082ノート

反応式

HRID 1181082 の反応式
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]=[O:5].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH2:11]([O:10][C:7]1[CH:8]=[CH:9][C:2]([Br:1])=[C:3]([CH:6]=1)[CH:4]=[O:5])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 3871792-Bromo-5-hydroxybenzaldehyde

生成物 1

HCID 108700245-(Benzyloxy)-2-bromobenzaldehyde

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A solution of 2-bromo-5-hydroxy-benzaldehyde (5.99 g, 29.8 mmol, Preparation 13 Step A) in DMF (50 mL) was treated with benzyl bromide (7.65 g, 44.7 mmol) and Cs2CO3 (15.1 g, 44.7 mmol). The resulting mixture was heated at 80° C. for 60 min and was quenched with water (200 mL). The mixture was extracted with EtOAc (2×100 mL), dried (Na2SO4), and concentrated to a residue, which was purified on silica gel chromatography (hexanes/EtOAc 9/1) to afford 5-benzyloxy-2-bromo-benzaldehyde as white solid in quantitative yield.

後処理

  1. customwas quenched with water (200 mL)
  2. extractionThe mixture was extracted with EtOAc (2×100 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated to a residue, which
  5. customwas purified on silica gel chromatography (hexanes/EtOAc 9/1)

出典と根拠

ORDレコード
ord-dbb74fd82e4a456ca3ea87b9e56004b9
出典データセット
uspto-grants-2007_10
特許番号
US07282501B2

反応ノート

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