3-Thiocresol → 2-Fluoro-6-m-tolylsulfanylbenzonitrile

HRID 2176981Notes

Reaction equation

HRID 2176981 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([SH:10])[CH:7]=[CH:8][CH:9]=1.[F:11][C:12]1[CH:19]=[CH:18][CH:17]=[C:16](F)[C:13]=1[C:14]#[N:15]>CN(C=O)C>[F:11][C:12]1[CH:19]=[CH:18][CH:17]=[C:16]([S:10][C:6]2[CH:5]=[C:4]([CH3:3])[CH:9]=[CH:8][CH:7]=2)[C:13]=1[C:14]#[N:15]

Participants

5

Reactant 3

HCID 79303-ThiocresolHCID 24758Sodium hydrideHCID 746952,6-Difluorobenzonitrile

Product 1

HCID 107766222-Fluoro-6-m-tolylsulfanylbenzonitrileYield 99.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a cold (ice water) suspension of sodium hydride (316 mg; 7.9 mmol) in anhydrous DMF (10 mL) is added a solution of 3-methylbenzenethiol (941 uL; 7.9 mmol) in anhydrous DMF (5 mL) over 10 minutes. After allowing to room temperature over 30 minutes, this solution is added to a cold (ice water) stirred solution of 2,6-difluorobenzonitrile (1 g; 7.2 mmol) in anhydrous DMF (15 mL), and allowed to room temperature over 3 hours. The reaction mixture is poured into ice water with vigorous stirring and the resulting precipitate is removed by filtration and dried under vacuum overnight to give 1.74 grams of 2-fluoro-6-m-tolylsulfanylbenzonitrile.

Workup

  1. waitallowed to room temperature over 3 hours
  2. customthe resulting precipitate is removed by filtration
  3. customdried under vacuum overnight

Sources & evidence

ORD record
ord-af1d74f506374a3c81a903fec33de244
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

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