Methyl iodide → Methyl 2-bromo-6-methylbenzoate

HRID 1097976

Reaction equation

HRID 1097976 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([OH:6])=[O:5].CI.[C:14](=O)([O-])O.[K+]>CN(C=O)C>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([O:6][CH3:14])=[O:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 516893Potassium BicarbonateHCID 27355892-Bromo-6-methylbenzoic acid

Product 1

HCID 11564857Methyl 2-bromo-6-methylbenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-bromo-6-methylbenzoic acid (5.02 g) and methyl iodide (2.9 mL) in N,N′-dimethylformamide (30 mL) was added powdered potassium hydrogen carbonate (4.67 g). The mixture was stirred at ambient temperature for 16 hours and concentrated. The concentrate was partitioned between ethyl acetate and water. The extract was washed with brine and concentrated, and the concentrate was purified by flash chromatography on silica gel with 60% ethyl acetate in hexanes.

Workup

  1. concentrationconcentrated
  2. customThe concentrate was partitioned between ethyl acetate and water
  3. washThe extract was washed with brine
  4. concentrationconcentrated
  5. customthe concentrate was purified by flash chromatography on silica gel with 60% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-95ffc6b7216c47e0afcf67899bff3076
Source dataset
uspto-grants-2012_03
Patent number
US08143284B2

Linked notes

Loading…