Methyl iodide → 4-Bromo-2-fluoro-benzoic acid methyl ester

HRID 2103811Notes

Reaction equation

HRID 2103811 reaction equation
CI.[Br:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[C:6]([F:13])[CH:5]=1.[C:14](=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>CN(C)C=O>[Br:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([O:10][CH3:14])=[O:9])=[C:6]([F:13])[CH:5]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 3026814-Bromo-2-fluorobenzoic acid

Product 1

HCID 113453114-Bromo-2-fluoro-benzoic acid methyl esterYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (1.49 mL, 24 mmol) was added to a suspension of 4-bromo-2-fluorobenzoic acid (4.38 g, 20 mmol) and sodium carbonate (6.36 g, 60 mmol) in dimethylformamide (50 mL), and the mixture was stirred overnight at room temperature. After completion of the reaction, ethyl acetate was added, and the mixture was washed with water and a saturated ammonium chloride aqueous solution. After drying over magnesium sulfate, concentration was carried out to obtain 4.50 g of the desired product as a colorless solid (yield 97%).

Workup

  1. additionwas added
  2. washthe mixture was washed with water
  3. dry with materialAfter drying over magnesium sulfate, concentration

Sources & evidence

ORD record
ord-1d2c0cbd64254cbfaf172a0266938955
Source dataset
uspto-grants-2009_08
Patent number
US07576115B2

Reaction notes

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