Methyl iodide → Methyl 3-Bromo-2-methylbenzoate

HRID 552389Notes

Reaction equation

HRID 552389 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[C:9]([CH3:17])=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([OH:13])=[O:12].IC>CC(C)=O>[CH3:1][O:12][C:11](=[O:13])[C:10]1[CH:14]=[CH:15][CH:16]=[C:8]([Br:7])[C:9]=1[CH3:17]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27355903-Bromo-2-methylbenzoic Acid

Product 1

HCID 12929135Methyl 3-Bromo-2-methylbenzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (5.46 g, 39.53 mmol) is added to a solution of 3-bromo-2-methyl-benzoic acid (5 g, 23.25 mmol) in acetone (50 mL). The suspension is stirred for 15 minutes at room temperature, then iodomethane (1.74 mL, 27.90 mmol) is added and the mixture is heated to 70° C. for 2.5 hours. The reaction mixture is filtered and evaporated to dryness. The crude product is purified by chromatography on a 50 g Isolute Flash Si II column, eluting with ethyl acetate/cyclohexane (5:95) to yield the title compound.

Workup

  1. temperaturethe mixture is heated to 70° C. for 2.5 hours
  2. filtrationThe reaction mixture is filtered
  3. customevaporated to dryness
  4. customThe crude product is purified by chromatography on a 50 g Isolute Flash Si II column
  5. washeluting with ethyl acetate/cyclohexane (5:95)

Sources & evidence

ORD record
ord-cc5a7abe89444b248416b0a9838804f6
Source dataset
uspto-grants-2011_05
Patent number
US07951818B2

Reaction notes

Loading…