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

HRID 1754105노트

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HRID 1754105 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
120 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-61ddc1b4bbbb488691d0cb31f7d942de
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09169209B2

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