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

HRID 2395052Notes

Reaction equation

HRID 2395052 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.C(OCC)(=O)C>CN(C=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 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 728635-Bromosalicylaldehyde

Product 1

HCID 7330872-(Benzyloxy)-5-bromobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-bromosalicylaldehyde (12 g), potassium carbonate (16.5 g) and benzyl bromide (7.8 ml) in DMF (50 ml) was stirred for 18 hours, poured into ethyl acetate (100 ml), washed with 0.05M HCl (100 ml), sodium bicarbonate (100 ml) and brine (100 ml), dried (sodium sulphate), filtered and evaporated. The residue was triturated with hexane/diethyl ether to give 2-benzyloxy-5-bromo-benzaldehyde (15.8 g) mp.70°-72° C.

Workup

  1. washwashed with 0.05M HCl (100 ml), sodium bicarbonate (100 ml) and brine (100 ml)
  2. dry with materialdried (sodium sulphate)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was triturated with hexane/diethyl ether

Sources & evidence

ORD record
ord-94d50fc8377248998528525ffd7c757a
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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