Potassium Carbonate → 4-((2-(Trifluoromethoxy)phenyl)thio)benzonitrile

HRID 1754105Notes

Reaction equation

HRID 1754105 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[SH:10].C([O-])([O-])=O.[K+].[K+].F[C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=1>CN(C=O)C.CCOC(C)=O>[F:12][C:2]([F:1])([F:11])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 145174-FluorobenzonitrileHCID 27607322-(Trifluoromethoxy)thiophenol

Product 1

HCID 709791104-((2-(Trifluoromethoxy)phenyl)thio)benzonitrileYield 74%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-(trifluoromethoxy)benzenethiol (1.035 g, 5.33 mmol) in DMF (15 mL) at 0° C. was added K2CO3 (921 mg, 6.66 mmol). The solution was warmed to ambient temperature over 10 min before 4-fluorobenzonitrile (613 mg, 5.06 mmol) was added at once. The mixture was heated to 120° C. for 16 hours, then was then cooled and poured onto ice. The mixture was diluted with EtOAc, the layers separated, and the organics were washed successively with sat. NaHCO3 and brine (2×). The organics were dried (MgSO4), filtered, and purified by Biotage SP1 (DCM/hexanes gradient) to afford 4-((2-(trifluoromethoxy)phenyl)thio)benzonitrile (1.098 g, 74%) as a golden oil.

Workup

  1. additionwas added at once
  2. temperaturewas then cooled
  3. additionpoured onto ice
  4. customthe layers separated
  5. washthe organics were washed successively with sat. NaHCO3 and brine (2×)
  6. dry with materialThe organics were dried (MgSO4)
  7. filtrationfiltered
  8. custompurified by Biotage SP1 (DCM/hexanes gradient)

Sources & evidence

ORD record
ord-61ddc1b4bbbb488691d0cb31f7d942de
Source dataset
uspto-grants-2015_10
Patent number
US09169209B2

Reaction notes

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