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

HRID 1930980Notes

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 B4(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-2dc05b95962e4ecb980da729328a3df3
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188139B2

Reaction notes

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