2-Bromo-6-chlorobenzoic acid → Methyl 2-bromo-6-chlorobenzoate

HRID 896719Notes

Reaction equation

HRID 896719 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4]([OH:6])=[O:5].[CH3:12][Si](C=[N+]=[N-])(C)C>CO>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4]([O:6][CH3:12])=[O:5]

Participants

4

Reactant 2

HCID 331252-Bromo-6-chlorobenzoic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 2759827Methyl 2-bromo-6-chlorobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-bromo-6-chlorobenzoic acid (17.7 g, 75.2 mmol) in methanol (200 mL) at 0° C. was added (trimethylsilyl)diazomethane (2M in hexanes, 100 mL, 0.200 mol). The solution was stirred at 0° C. for 1.5 hours, then warmed to room temperature and washed with aqueous sodium bicarbonate and brine, dried over Na2SO4, filtered and concentrated. The residue was subjected to silica gel chromatography eluted with 0-5% ethyl acetate in hexanes to provide methyl 2-bromo-6-chlorobenzoate as a pale yellow oil that gave proton NMR spectra consistent with theory.

Workup

  1. temperaturewarmed to room temperature
  2. washwashed with aqueous sodium bicarbonate and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washeluted with 0-5% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-461a62a34e8f4c24b67ae45093547b47
Source dataset
uspto-grants-2005_07
Patent number
US06919343B2

Reaction notes

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