4-Fluorobenzenesulfonyl chloride → 4-fluorobenzenesulfinic acid sodium salt
Reaction equation
FC1C=CC(S)=CC=1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1.S([O-])(O)=O.[Na+:24]>>[F:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([O-:18])=[O:17])=[CH:12][CH:11]=1.[Na+:24]Participants
4
Procedure
It has now been found that 4-fluorothiophenol can be prepared in an advantageous manner if 4-fluorobenzenesulphonyl chloride is first reacted with sodium hydrogen sulphite solution to give a solution of sodium 4-fluorobenzenesulphinate, then this solution is reduced with sulphur dioxide to give 4,4'-difluorodiphenyl disulphide and this is finally reacted with sodium borohydride in a water-miscible inert organic solvent to give 4-fluorothiophenol (sodium salt). 4-Fluorothiophenol can be isolated from this sodium salt solution after distilling off the solvent, for example by acidifying the solution, separating off the organic phase forming and if appropriate purifying still further.
Sources & evidence
- ORD record
- ord-0d89c01f87304cff9af996fc48a5ec42
- Source dataset
- uspto-grants-1997_08
- Patent number
- US05659088
Reaction notes
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