Methanol → 2-(Benzylthio)-6-(trifluoromethyl)pyridine

HRID 537255노트

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HRID 537255 반응식
[H-].[Na+].[C:3]1([CH2:9][SH:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.F[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[N:13]=1.CO>O1CCCC1.ClCCl.O>[CH2:9]([S:10][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[N:13]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

참가 물질

8

반응물 4

HCID 887MethanolHCID 7509Benzyl mercaptanHCID 24758Sodium hydrideHCID 27365012-Fluoro-6-(trifluoromethyl)pyridine

생성물 1

HCID 722130812-(Benzylthio)-6-(trifluoromethyl)pyridine수율 69.4%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a suspension of sodium hydride (0.170 g, 4.24 mmol) in tetrahydrofuran (10 mL) was added phenylmethanethiol (0.338 ml, 2.88 mmol) dropwise at 0° C. The reaction mixture was stirred at 0° C. for 15 minutes then 2-fluoro-6-(trifluoromethyl)pyridine (0.365 ml, 3.03 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 30 minutes. Methanol (1 mL) was added carefully and the reaction mixture was stirred at 0° C. for a further 10 minutes then water (5 mL) and dichloromethane (10 mL) were added. The organic layer was recovered using a phase separator cartridge then concentrated in vacuo to give 2-(benzylthio)-6-(trifluoromethyl)pyridine (538 mg) as a colourless oil. LCMS (Method F, ES-API): RT 2.80 min, m+H=270.1.

후처리

  1. stirringThe reaction mixture was stirred at 0° C. for 30 minutes
  2. stirringthe reaction mixture was stirred at 0° C. for a further 10 minutes
  3. customThe organic layer was recovered
  4. concentrationthen concentrated in vacuo

출처 및 근거

ORD 기록
ord-1a762b3af496432996c4594a971641df
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859774B2

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