Methanol → Methyl 3-bromo-4-methylbenzoate

HRID 735855Notes

Reaction equation

HRID 735855 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].O=S(Cl)Cl.[CH3:16]O>>[CH3:16][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([CH3:11])=[C:2]([Br:1])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 821303-Bromo-4-methylbenzoic acid

Product 1

HCID 7015747Methyl 3-bromo-4-methylbenzoateYield 95%

Procedure

A mixture of 3-bromo-4-methylbenzoic acid (40 g, 0.186 mol) and SOCl2 (88 g, 0.74 mol) in methanol (600 mL) was refluxed for 12 h. The solvent was distilled off and the crude residue was diluted with ethyl acetate (50 mL). The ethyl acetate layer was washed with 10% NaHCO3 solution, water, brine and dried. The solvent was removed under vacuum to give methyl-3-bromo-4-methylbenzoate (40 g, 95%) as a solid.

Workup

  1. temperaturewas refluxed for 12 h
  2. distillationThe solvent was distilled off
  3. additionthe crude residue was diluted with ethyl acetate (50 mL)
  4. washThe ethyl acetate layer was washed with 10% NaHCO3 solution, water, brine
  5. customdried
  6. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-ce1e8038a98f4d2ca22495b9199c4a5d
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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