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

HRID 1181082Notes

Reaction equation

HRID 1181082 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 108700245-(Benzyloxy)-2-bromobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-dbb74fd82e4a456ca3ea87b9e56004b9
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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