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

HRID 1181082노트

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HRID 1181082 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 108700245-(Benzyloxy)-2-bromobenzaldehyde

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-dbb74fd82e4a456ca3ea87b9e56004b9
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07282501B2

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