Thiophenol → 4-Bromo-2-(phenylsulfanyl)benzonitrile

HRID 425289Notes

Reaction equation

HRID 425289 reaction equation
[H-].[Na+].[C:3]1([SH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13](F)[CH:12]=1.[OH-].[Na+]>CN(C=O)C>[Br:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13]([S:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH:12]=1

Participants

6

Reactant 4

HCID 7969ThiophenolHCID 14798Sodium HydroxideHCID 24758Sodium hydride2×HCID 7360294-Bromo-2-fluorobenzonitrile

Product 1

HCID 577253024-Bromo-2-(phenylsulfanyl)benzonitrileYield 96.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (2.40 g, 60 mmol) (60% by wt) was weighed into a flask and washed with several hexane rinsings. The hexanes were decanted and discarded and 20 mL DMF was added to the flask. A DMF-solution of benzenethiol (5.1 mL, 50 mmol in 50 mL DMF) was added dropwise to the NaH mixture and stirred at room temperature. To 4-bromo-2-fluoro-benzonitrile (10.0 g, 50 mmol) in 40 mL DMF) was added benzenethiophenoxide (described above), dropwise, over 30 minutes. Upon complete addition, the reaction was stirred at room temperature for 20 min. At that time, the mixture was poured into cold 1 N NaOH. A precipitate formed and was collected by vacuum filtration to give 14.0 g (48.4 mmol) of Compound 1h.

Workup

  1. washwashed with several hexane rinsings
  2. customThe hexanes were decanted
  3. addition20 mL DMF was added to the flask
  4. additionUpon complete addition
  5. stirringthe reaction was stirred at room temperature for 20 min
  6. customA precipitate formed
  7. filtrationwas collected by vacuum filtration

Sources & evidence

ORD record
ord-ec33a9391ca24958b9817d64a2509aa7
Source dataset
uspto-grants-2012_01
Patent number
US08106207B2

Reaction notes

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