Stannous chloride dihydrate → 2-Fluoro-2'-(methylthio)biphenyl-5-ylamine

HRID 1061790

반응식

HRID 1061790 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17][CH3:18].O.O.[Sn](Cl)Cl>O1CCCC1.C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17][CH3:18]

참가 물질

5

반응물 2

HCID 61436Stannous chloride dihydrateHCID 222852772-Fluoro-2'-methylthio-5-nitrobiphenyl

생성물 1

HCID 222852932-Fluoro-2'-(methylthio)biphenyl-5-ylamine수율 98%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 2-fluoro-2′-methylthio-5-nitrobiphenyl (6.00 g, 22.8 mmol) in tetrahydrofuran (50 mL) and ethanol (50 mL) was treated with tin(II) chloride dihydrate (25.70 g, 113.9 mmol) and the mixture was stirred at ambient temperature for 25 h. The solvent was evaporated and the residue stirred with 2 N sodium hydroxide solution (240 mL) for 18 h. The resulting suspension was extracted with dichloromethane (3×200 mL). The combined organic extracts were dried over anhydrous magnesium sulphate and evaporated. The residue was purified by flash chromatography on silica gel eluting with 35% ethyl acetate in isohexane to afford 2-fluoro-2′-(methylthio)biphenyl-5-ylamine as a white solid (5.20 g, 98%): δH (360 MHz, CDCl3) 2.39 (3H, s), 6.60 (1H, dd, J 6 and 3), 6.64-6.68 (1H, m), 6.94 (1H, t, J 9), 7.19-7.20 (2H, m), 7.30 (1H, d, J 8), 7.33-7.37 (1H, m).

후처리

  1. customThe solvent was evaporated
  2. stirringthe residue stirred with 2 N sodium hydroxide solution (240 mL) for 18 h
  3. extractionThe resulting suspension was extracted with dichloromethane (3×200 mL)
  4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulphate
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel eluting with 35% ethyl acetate in isohexane

출처 및 근거

ORD 기록
ord-b858d71b3d0f4115ac09a4c6e7afbd38
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06960598B2

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