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

HRID 1881544Notes

Reaction equation

HRID 1881544 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-4e877a15114040e698d6e6058d073282
Source dataset
uspto-grants-2012_11
Patent number
US08318796B2

Reaction notes

Loading…