Methyl iodide → Methyl 3-Bromo-2-methylbenzoate

HRID 577460Notes

Reaction equation

HRID 577460 reaction equation
[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[C:12](=O)([O-])[O-].[Cs+].[Cs+].IC.C(OCC)(=O)C>CN(C=O)C>[Br:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH3:12])=[O:6]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 27355903-Bromo-2-methylbenzoic Acid

Product 1

HCID 12929135Methyl 3-Bromo-2-methylbenzoateYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-bromo-2-methylbenzoic acid (2.98 g, 13.9 mmol) in DMF (20 mL) was treated with cesium carbonate (4.56 g, 13.9 mmol) and iodomethane (0.900 mL, 14.4 mmol). The reaction mixture was stirred at room temperature for 3 hours. The solution was poured into ethyl acetate and washed with water (3×) and brine. The ethyl acetate layer was concentrated under vacuum to give methyl 3-bromo-2-methylbenzoate (Cpd FF, 2.70 g, 85% yield) as a clear oil.

Workup

  1. washwashed with water (3×) and brine
  2. concentrationThe ethyl acetate layer was concentrated under vacuum

Sources & evidence

ORD record
ord-47d2ab5d34e74764a6d95fe02165b3fd
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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