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

HRID 584994Notes

Reaction equation

HRID 584994 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CC(C)=O>[CH2:11]([O:10][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:9][C:6]=1[CH:7]=[O:8])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 728635-Bromosalicylaldehyde

Product 1

HCID 7330872-(Benzyloxy)-5-bromobenzaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a manner similar to that of Example 75(a), by reacting g (150 mmol) of 5-bromo-2-hydroxy-benzaldehyde and 17.8 ml (150 mmol) of benzyl bromide in 300 ml of acetone, and after purification by chromatography on a column of silica eluted with a heptane/ethyl acetate mixture (8/2), 22.8 g (52%) of the expected product are obtained in the form of a yellow solid.

Workup

  1. customafter purification by chromatography on a column of silica
  2. washeluted with a heptane/ethyl acetate mixture (8/2), 22.8 g (52%) of the expected product
  3. customare obtained in the form of a yellow solid

Sources & evidence

ORD record
ord-4ac83e6499ff4bbf831545b724d0c5b6
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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