Dimethylformamide → Methyl 4-chloro-3-(methylsulfonyl)benzoate

HRID 1845142Notes

Reaction equation

HRID 1845142 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5](C(O)=O)=[CH:4][C:3]=1[S:11]([OH:13])=[O:12].[C:14](=[O:17])([O-])[O-].[K+].[K+].CN(C)[CH:22]=[O:23].[CH3:25]I>O>[CH3:14][O:17][C:22](=[O:23])[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[C:3]([S:11]([CH3:25])(=[O:12])=[O:13])[CH:4]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2645656HCID 2645656, compound

Product 1

HCID 10490815Methyl 4-chloro-3-(methylsulfonyl)benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A round bottom flask was charged with 4-chloro-3-sulfinobenzoic acid (12 g, 54.0 mmol), potassium carbonate (15.4 g, 109 mmol) and N,N-dimethylformamide (170 mL). Methyl iodide (16.1 mL, 218 mmol) was added slowly and the reaction was stirred for 4 hours. The reaction mixture was then diluted with water and extracted with EtOAc. The combined organic layers were concentrated under reduced pressure to get the intermediate methyl-4-chloro-3-(methylsulfonyl)benzoate as an off white solid. This was dissolved in methanol (100 mL) and 6N sodium hydroxide (50 mL) was added and the reaction was stirred for 3 hours. Methanol was removed under reduced pressure and water was added to the residue. The resulting mixture was then acidified with 2N HCl at 0° C. and the solid formed was filtered and dried to get the title compound as a white solid.

Workup

  1. extractionextracted with EtOAc
  2. concentrationThe combined organic layers were concentrated under reduced pressure

Sources & evidence

ORD record
ord-47b871d2c92848a7b8bc8711c6e5f580
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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