Hydrochloric Acid → 2-Isobutylsulfanyl-5-methanesulfonyl-benzoic acid

HRID 1352266Notes

Reaction equation

F[C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:21][CH:22]([CH3:25])[CH2:23][SH:24].Cl>CN(C)C=O>[CH2:23]([S:24][C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])[CH:22]([CH3:25])[CH3:21]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 4.58 mmol 2-fluoro-5-methanesulfonyl-benzoic acid (Example A14(b)) in 6 ml N,N-dimethylformamide were added 13.8 mol cesium carbonate and 9.97 mmol 2-methyl-1-propanethiol and the mixture was stirred at 90° C. for 30 min. The reaction mixture was then cooled to room temperature and acidified to pH1 by addition of hydrochloric acid before being extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo to afford the title compound as a white solid which was used in the next step without further purification (yield 99%). MS (m/e): 287.0 ([M−H]−, 100%).

Workup

temperatureThe reaction mixture was then cooled to room temperature
extractionbefore being extracted three times with ethyl acetate
dry with materialThe combined organic phases were dried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-2e3be9a8fa404a19be7a6945ff66c2c1
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07220744B2

Reaction notes

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