Methanol → Methyl 4-bromo-2-methylbenzoate

HRID 884638Notes

Reaction equation

HRID 884638 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]O>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:12])=[O:7])=[C:4]([CH3:11])[CH:3]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 995704-Bromo-2-methylbenzoic acid

Product 1

HCID 22031226Methyl 4-bromo-2-methylbenzoateYield 89%

Procedure

To a round bottomed flask was added MeOH (25 mL) and commercially available 4-bromo-2-methyl benzoic acid (7.0 g, 32.8 mmol). Then 4N HCL/dioxanes (25 mL) was added to the insoluble mixture and stirred under reflux for 3 h. The reaction was concentrated. EtOAc and H2O were added to the slurry and partitioned. The EtOAc layer was washed with NaHCO3 (sat.) 3×, washed with brine and dried with Na2SO4 and concentrated to give methyl 4-bromo-2-methylbenzoate as a light brown oil (6.7 g, 89% yield).

Workup

  1. temperatureunder reflux for 3 h
  2. concentrationThe reaction was concentrated
  3. additionEtOAc and H2O were added to the slurry
  4. custompartitioned
  5. washThe EtOAc layer was washed with NaHCO3 (sat.) 3×
  6. washwashed with brine
  7. dry with materialdried with Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-2819b18bfab447fda7133affecf7ee68
Source dataset
uspto-grants-2012_08
Patent number
US08242129B2

Reaction notes

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