Water → 2-(Benzyloxy)-5-bromobenzaldehyde

HRID 2406044Notes

Reaction equation

HRID 2406044 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 for 40 min under ice-cooling, and further at room temperature for 15 hr. Water was added to the reaction mixture, the mixture was extracted with ethyl acetate, and the extract was washed successively with 0.1M aqueous sodium hydroxide solution and 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
  3. waitfurther at room temperature for 15 hr
  4. extractionthe mixture was extracted with ethyl acetate
  5. washthe extract was washed successively with 0.1M aqueous sodium hydroxide solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-29c69880ca304070a0de87e081f8c81e
Source dataset
uspto-grants-2014_08
Patent number
US08809304B2

Reaction notes

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