Benzyl Bromide → Benzyl 2-formylbenzoate

HRID 446500

Reaction equation

HRID 446500 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([O-:7])=[O:6])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O.C(OCC)(=O)C>[CH:1]([C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([O:7][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:6])=[O:2]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 50829392-Formylbenzoate

Product 1

HCID 246096Benzyl 2-formylbenzoateYield 99.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Formylbenzoate (500 mg, 3.33 mmol) was dissolved in N,N-dimethylformamide (3 mL), potassium carbonate (553 mg, 4.00 mmol) and benzyl bromide (0.396 mL, 3.33 mmol) were added, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate, and then the organic layer was washed with water (×3) and saturated sodium chloride solution. The organic layer was dried with anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure to give the title compound (795 mg; yield, 99%) as a colorless oily substance.

Workup

  1. washthe organic layer was washed with water (×3) and saturated sodium chloride solution
  2. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9e3b1979f2804321b3168eade90f100d
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Linked notes

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