Benzyl mercaptan → 5-(Benzylthio)-2-(4-cyano-3-chlorophenoxy)-3-fluorobenzonitrile

HRID 2178136Notes

Reaction equation

HRID 2178136 reaction equation
Br[C:2]1[CH:3]=[C:4]([F:20])[C:5]([O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[C:13]([Cl:19])[CH:12]=2)=[C:6]([CH:9]=1)[C:7]#[N:8].[CH2:21]([SH:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CCOC(C)=O.O.C(=O)([O-])O.[Na+]>[CH2:21]([S:28][C:2]1[CH:3]=[C:4]([F:20])[C:5]([O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[C:13]([Cl:19])[CH:12]=2)=[C:6]([CH:9]=1)[C:7]#[N:8])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 2

HCID 7509Benzyl mercaptanHCID 1176532065-Bromo-2-(4-cyano-3-chlorophenoxy)-3-fluorobenzonitrile

Product 1

HCID 1176533775-(Benzylthio)-2-(4-cyano-3-chlorophenoxy)-3-fluorobenzonitrileYield 28%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

The title compound was prepared according to the method described for Preparation at reflux using 5-bromo-2-(4-cyano-3-chlorophenoxy)-3-fluorobenzonitrile (Preparation 41) and benzyl mercaptan. The reaction was allowed to cool to room temperature and diluted with EtOAc (100 mL), water (50 mL) and saturated aqueous sodium hydrogen carbonate solution (100 mL). The organic was separated and the aqueous was re-extracted with EtOAc (2×100 mL). The combined organic layers were washed with brine (100 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The residue was absorbed onto silica and purified by silica gel column chromatography eluting with 10% EtOAc in heptanes to afford the title compound as a yellow solid (115 mg, 28%).

Workup

  1. customThe title compound was prepared
  2. customdescribed for Preparation
  3. temperatureat reflux
  4. customThe organic was separated
  5. extractionthe aqueous was re-extracted with EtOAc (2×100 mL)
  6. washThe combined organic layers were washed with brine (100 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was absorbed onto silica
  11. custompurified by silica gel column chromatography
  12. washeluting with 10% EtOAc in heptanes

Sources & evidence

ORD record
ord-2fc45e53ba684423a69daebca12b5f59
Source dataset
uspto-grants-2015_06
Patent number
US09067922B2

Reaction notes

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