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

HRID 1061790

反応式

HRID 1061790 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b858d71b3d0f4115ac09a4c6e7afbd38
出典データセット
uspto-grants-2005_11
特許番号
US06960598B2

関連ノート

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