Methyl iodide → 2,6-Difluoro-3-(methylsulfonyl)benzoic acid

HRID 1820768Notes

Reaction equation

HRID 1820768 reaction equation
[C:1](=O)([O-])[O-].[Na+].[Na+].[F:7][C:8]1[C:16]([S:17]([OH:19])=[O:18])=[CH:15][CH:14]=[C:13]([F:20])[C:9]=1[C:10]([OH:12])=[O:11].CI>CO.O>[F:7][C:8]1[C:16]([S:17]([CH3:1])(=[O:19])=[O:18])=[CH:15][CH:14]=[C:13]([F:20])[C:9]=1[C:10]([OH:12])=[O:11]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 690401022,6-Difluoro-3-sulfino-benzoic acid

Product 1

HCID 431409352,6-Difluoro-3-(methylsulfonyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A suspension of 18 mmol sodium carbonate and 9 mmol 2,6-Difluoro-3-sulfino-benzoic acid in 30 ml of methanol was stirred at room temperature for 30 min, then heated to 60° C. 24 mmol of methyl iodide were added and the reaction mixture heated overnight at 60° C. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was discarded and the aqueous phase acidified by addition of concentrated hydrochloric acid. Extraction with ethyl acetate yielded the title compound as a slightly brownish solid. MS (m/e): 235.1 (M−H, 16%)

Workup

  1. temperatureheated to 60° C
  2. temperaturethe reaction mixture heated overnight at 60° C
  3. extractionextracted with ethyl acetate
  4. additionthe aqueous phase acidified by addition of concentrated hydrochloric acid
  5. extractionExtraction with ethyl acetate

Sources & evidence

ORD record
ord-a3ad6988b35c44f7b2a6956de04b94d2
Source dataset
uspto-grants-2009_10
Patent number
US07605163B2

Reaction notes

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