Methanol → Methyl 4-bromo-2-methylbenzoate

HRID 1351998Notes

Reaction equation

HRID 1351998 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.S(=O)(=O)(O)O.[CH3:17]O>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:17])=[O:7])=[C:4]([CH3:11])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 995704-Bromo-2-methylbenzoic acid

Product 1

HCID 22031226Methyl 4-bromo-2-methylbenzoateYield 78%

Procedure

A mixture of 4-bromo-2-methylbenzoic acid (14.77 g, 68.7 mmol) and sulfuric acid (5 mL) in methanol (200 mL) was heated at reflux for 3 h. The solvent was evaporated and dichloromethane (200 mL) was added. The solution was washed with water, 1 M NaOH, and brine (200 mL each), dried (MgSO4), filtered and evaporated to give 4-bromo-2-methylbenzoic acid, methyl ester (12.21 g, 78%) as a colorless liquid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. customThe solvent was evaporated
  4. additiondichloromethane (200 mL) was added
  5. washThe solution was washed with water, 1 M NaOH, and brine (200 mL each)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-626f47aa9453474280a7d18b5eb90551
Source dataset
uspto-grants-2007_05
Patent number
US07217728B2

Reaction notes

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