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

HRID 225698Notes

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]([SH:24])[CH3:23].Cl>CN(C)C(=O)C>[CH:22]([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])([CH3:23])[CH3:21]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 4.58 mmol 2-fluoro-5-methanesulfonyl-benzoic acid in 6 ml N,N-dimethylacetamide were added 15.2 mol cesium carbonate and 10.1 mmol 2-propanethiol and the mixture was stirred at 90° C. for 3 h. 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 light yellow liquid which was used in the next step without further purification (yield 99%). EI-MS (m/e): 274.1 (M+, 35%), 232.1 ([M−C3H6]+, 30%, 214.1 (M−C3H6−H2O)+, 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-383aaf719c074e3f9287dcc6d625cb20
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557114B2

Reaction notes

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