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

HRID 840297Notes

Reaction equation

HRID 840297 reaction equation
[Br:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C.C(OCC)(=O)C>[CH2:17]([O:10][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:9][C:6]=1[CH:7]=[O:8])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 728635-Bromosalicylaldehyde

Product 1

HCID 7330872-(Benzyloxy)-5-bromobenzaldehydeYield 90.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-bromosalicylaldehyde (12.0 g, 59.7 mmol) in DMF (50 ml) was treated with K2CO3 (16.5 g, 120 mmol) and benzyl bromide (11.2 g, 65.6 mmol). The reaction was stirred at ambient temperature for 18 hours, diluted with ethyl acetate and filtered. The filtrate was washed with HCl (0.05 M), saturated aqueous sodium hydrogen carbonate and brine. The organic phase was dried (Na2SO4) and evaporated and the residue triturated with hexane/ethyl ether. The product was filtered off to give 2-benzyloxy-5-bromobenzaldehyde as a white solid (15.8 g, 90%) m.p. 70-72 ° C.

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with HCl (0.05 M), saturated aqueous sodium hydrogen carbonate and brine
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customevaporated
  5. customthe residue triturated with hexane/ethyl ether
  6. filtrationThe product was filtered off

Sources & evidence

ORD record
ord-130dd032dabf45f8b739dfc93cf03341
Source dataset
uspto-grants-2002_04
Patent number
US06365603B1

Reaction notes

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