Water → 2-(Benzyloxy)-5-bromobenzaldehyde

HRID 1093402Notes

Reaction equation

HRID 1093402 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.O>CN(C)C=O>[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 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 728635-Bromosalicylaldehyde

Product 1

HCID 7330872-(Benzyloxy)-5-bromobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 5-bromosalicylaldehyde (25.0 g) and potassium carbonate (51.4 g) in N,N-dimethylformamide (250 ml) was added benzyl bromide (15.4 ml) under ice-cooling, and the mixture was stirred under ice-cooling for 40 min, and further at room temperature for 15 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate, washed with 0.1M aqueous sodium hydroxide solution and then saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was suspended in hexane (200 ml) and collected by filtration to give the object product (32.7 g) as a pale-yellow powder.

Workup

  1. temperaturecooling
  2. temperaturecooling for 40 min
  3. extractionthe mixture was extracted with ethyl acetate
  4. washwashed with 0.1M aqueous sodium hydroxide solution
  5. dry with materialsaturated brine, and dried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-8dd4b02305c944f29b04bae6bc792d79
Source dataset
uspto-grants-2012_03
Patent number
US08129361B2

Reaction notes

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