4-Bromo-2-methylbenzoic acid → Methyl 4-bromo-2-methylbenzoate

HRID 1442806Notes

Reaction equation

HRID 1442806 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[CH:3]=1.[CH3:12]C1C=CC(S(O)(=O)=O)=CC=1.O>CO>[CH3:12][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][C:4]=1[CH3:11]

Participants

4

Reactant 2

HCID 995704-Bromo-2-methylbenzoic acidHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 22031226Methyl 4-bromo-2-methylbenzoateYield 1,135%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-bromo-2-methylbenzoic acid (2.0 g, 9.3 mmol) in methanol (20 mL) was added p-TsOH.H2O (90 mg, 0.50 mmol). The mixture was heated at reflux overnight. Methanol was evaporated and the residue was purified by chromatography on silica gel (3% ethyl acetate in petroleum ether) to afford 4-bromo-2-methyl-benzoic acid methyl ester (1.3 g, 61%). 1H NMR (CDCl3, 300 MHz) δ 7.78 (d, J=8.4 Hz, 1H), 7.41-7.36 (m, 2H), 3.89 (s, 3H), 2.57 (s, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. customMethanol was evaporated
  4. customthe residue was purified by chromatography on silica gel (3% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-617874c62c4849699802a5b9913ad054
Source dataset
uspto-grants-2010_02
Patent number
US07659268B2

Reaction notes

Loading…