Methanol → Methyl 4-bromo-alpha-hydroxybenzeneacetate

HRID 547092

Reaction equation

HRID 547092 reaction equation
C[Si](C=[N+]=[N-])(C)C.[CH3:8]CCCCC.[Br:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([OH:25])[C:22]([OH:24])=[O:23])=[CH:17][CH:16]=1.CO>C1C=CC=CC=1>[CH3:8][O:23][C:22](=[O:24])[CH:21]([C:18]1[CH:17]=[CH:16][C:15]([Br:14])=[CH:20][CH:19]=1)[OH:25]

Participants

6

Reactant 4

HCID 887MethanolHCID 8058HexaneHCID 97930p-Bromomandelic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 14571696Methyl 4-bromo-alpha-hydroxybenzeneacetateYield 93.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of trimethylsilyldiazomethane in hexane (2 M, 1.4 mL, 2.8 mmol) was added to a solution of 4-bromo-phenyl-hydroxy-acetic acid (506 mg, 2.19 mmol) in benzene (2.1 mL)-methanol (1.0 mL) under cooling with ice, and the mixture was stirred at room temperature for five minutes. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=3/1) to give the title compound (500 mg, 93%).

Workup

  1. temperatureunder cooling with ice
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-b20975e893d9451080f5f154d764a445
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Linked notes

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