Benzyl mercaptan → 2-(Benzylthio)-6-iodobenzonitrile

HRID 560945Notes

Reaction equation

HRID 560945 reaction equation
CC(C)([O-])C.[K+].[C:7]1([CH2:13][SH:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.F[C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([I:24])[C:17]=1[C:18]#[N:19].[Cl-].[NH4+]>C1COCC1>[CH2:13]([S:14][C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([I:24])[C:17]=1[C:18]#[N:19])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 7509Benzyl mercaptanHCID 25517Ammonium ChlorideHCID 5227222-Fluoro-6-iodobenzonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 248083272-(Benzylthio)-6-iodobenzonitrileYield 68.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of potassium tert-butoxide (1.12 g, 10.0 mmol) and phenyl-methanethiol (1.24 g, 10 mmol) in THF (30 mL) at room temperature was stirred for 10 minutes before treating with 2-fluoro-6-iodo-benzonitrile (2.47 g, 10 mmol). The solution was stirred for 1 hour at room temperature, poured into a saturated ammonium chloride solution and filtered. The filter cake was recrystallized from hexanes to provide 2.41 g (53% yield) of the desired product. MS (ESI(−)) m/e 350.0 (M−H)−.

Workup

  1. stirringThe solution was stirred for 1 hour at room temperature
  2. filtrationfiltered
  3. customThe filter cake was recrystallized from hexanes

Sources & evidence

ORD record
ord-37857df234dd4e61b53e55376e7cd0d4
Source dataset
uspto-grants-2011_11
Patent number
US08063091B2

Reaction notes

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