p-Chlorothiophenol → 2-[(4-Chlorophenyl)sulfanyl]-6-fluorobenzonitrile

HRID 1364387Notes

Reaction equation

HRID 1364387 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[H-].[Na+].[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>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:16]2[CH:17]=[CH:18][CH:19]=[C:12]([F:11])[C:13]=2[C:14]#[N:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7815p-ChlorothiophenolHCID 24758Sodium hydrideHCID 746952,6-Difluorobenzonitrile

Product 1

HCID 27372962-[(4-Chlorophenyl)sulfanyl]-6-fluorobenzonitrileYield 87.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

4-Chlorobenzenethiol (1.14 g; 7.9 mmol) in anhydrous DMF is added over 1 hour to an ice-cooled suspension of sodium hydride, 60% dispersion in mineral oil (316 mg; 7.9 mmol), in anhydrous DMF. The reaction is allowed to room temperature over 30 minutes. This material is then added over 30 minutes to an ice-cooled solution of 2,6-difluorobenzonitrile (1.0 g; 7.2 mmol) in anhydrous DMF. After the addition the reaction is allowed to room temperature and stirred for 2 hours. The reaction mixture is then poured slowly into vigorously stirred ice water to give a white paste, which becomes solid with continued stirring. The solid is filtered, washed with water, and dried under vacuum at 30° C. overnight to yield 1.66 grams of 2-(4-chlorophenylsulfanyl)-6-fluorobenzonitrile.

Workup

  1. temperaturecooled
  2. additionAfter the addition the reaction
  3. customis allowed to room temperature
  4. customto give a white paste, which
  5. filtrationThe solid is filtered
  6. washwashed with water
  7. customdried under vacuum at 30° C. overnight

Sources & evidence

ORD record
ord-68782d8f3fd241a38fc6a54bb350ed61
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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