Benzyl mercaptan → Benzyl(3-bromo-2-chlorophenyl)sulfane

HRID 76803Notes

Reaction equation

HRID 76803 reaction equation
[C:1]1([CH2:7][SH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[Cs+].[Cs+].[Br:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18](F)[C:17]=1[Cl:23]>CN(C=O)C.C(OCC)(=O)C.O>[CH2:7]([S:8][C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([Br:15])[C:17]=1[Cl:23])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 7509Benzyl mercaptanHCID 10796Cesium carbonateHCID 37393011-Bromo-2-chloro-3-fluorobenzene

Product 1

HCID 66911177Benzyl(3-bromo-2-chlorophenyl)sulfane

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 22728543Water ethylacetateSolvent

Procedure

To stirred phenyl-methanethiol (14.8 g, 119.36 mmol) in 175 ml DMF was added Cs2CO3 (38.89 g, 119.36 mmol) under argon. After 10 min. 1-bromo-2-chloro-3-fluoro-benzene (25 g, 119.36 mmol) in 25 ml DMF was added and stirring was continued overnight at RT and then 3 h at 80° C. After cooling the mixture was diluted with ethyl acetate/water and washed subsequently with 1 N HCl and brine. The organic layer was dried with MgSO4, filtered and evaporated. Purification by chromatography on silica gel yielded 22 g (59%) as an amorphous, colorless solid.

Workup

  1. waitwas continued overnight at RT
  2. custom3 h
  3. customat 80° C
  4. temperatureAfter cooling the mixture
  5. washwashed subsequently with 1 N HCl and brine
  6. dry with materialThe organic layer was dried with MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customPurification by chromatography on silica gel
  10. customyielded 22 g (59%) as an amorphous, colorless solid

Sources & evidence

ORD record
ord-9df104e0df9f402e818fccf9e21a172f
Source dataset
uspto-grants-2014_09
Patent number
US08835653B2

Reaction notes

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