Methanol → Methyl 2-bromo-4-methylbenzoate

HRID 1037072Notes

Reaction equation

HRID 1037072 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:16]O>>[Br:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:16])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 2262922-Bromo-4-methylbenzoic acid

Product 1

HCID 21779704Methyl 2-bromo-4-methylbenzoateYield 97%

Procedure

To a solution of 2-bromo-4-methylbenzoic acid (21.5 g, 100 mmol) in MeOH (250 mL) was added thionyl chloride (10.9 mL, 150 mmol) dropwise and then the reaction mixture was refluxed for 4 h. MeOH was distilled out and water was added. It was extracted with EA and the organic layer was washed with saturated sodium bicarbonate solution, brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel eluted with PE-EA (20:1) to give methyl 2-bromo-4-methylbenzoate (22.3 g, yield 97%) as colorless oil.

Workup

  1. temperaturethe reaction mixture was refluxed for 4 h
  2. distillationMeOH was distilled out and water
  3. additionwas added
  4. extractionIt was extracted with EA
  5. washthe organic layer was washed with saturated sodium bicarbonate solution, brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography over silica gel
  10. washeluted with PE-EA (20:1)

Sources & evidence

ORD record
ord-2002bffbd5054f1a8e857ee6014b2d1d
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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