2-Mercaptobenzoic Acid → 2-((2,2,2-Trifluoroethyl)sulfanyl)benzoic acid
Reaction equation
[OH-].[Na+].[SH:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7].Cl[CH2:14][C:15]([F:18])([F:17])[F:16]>CN(C)C=O>[F:16][C:15]([F:18])([F:17])[CH2:14][S:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A two-necked flask was charged under nitrogen with 45 ml of dimethylformamide and 16 g of a 50% strength by weight aqueous sodium hydroxide solution. After addition of 15 g of 2-mercaptobenzoic acid, 18 g of chlorotrifluoroethane were passed in at 0° C. and the reaction mixture was then transferred into a stirred autoclave. The mixture was heated at 100° C. for 12 hours (maximum pressure: 2.5 bar), allowed to cool and the crude product was then precipitated by addition of concentrated hydrochloric acid. The dried crude product was recrystallized from hot formic acid, giving 5.3 g of 2-(2',2',2'-trifluoroethylthio)benzoic acid having a melting point of 226°-227° C.
Workup
- customwere passed in at 0° C.
- temperatureto cool
- customthe crude product was then precipitated by addition of concentrated hydrochloric acid
- customThe dried crude product
- customwas recrystallized from hot formic acid
Sources & evidence
- ORD record
- ord-23399a1f1dc446e4ad0a9002660202c2
- Source dataset
- uspto-grants-1996_07
- Patent number
- US05534634
Reaction notes
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