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

HRID 586272

反応式

HRID 586272 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[C:3]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[S:17][CH3:18])=[CH:4][C:5]([NH2:8])=[CH:6][CH:7]=1

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 (MgSO4) and evaporated. The residue was purified by flash chromatography (silica gel, 35% EtOAc/isohexane) to give 5.20 g (98%) of the title compound as a white solid: 1H NMR (360 MHz, CDCl3) δ 2.39 (3H, s), 6.60 (1H, dd, J 2.8, 6.0 Hz), 6.646.68 (1H, m), 6.94 (1H, t, J 8.9 Hz), 7.19-7.20 (2H, m), 7.30 (1H, d, J 7.7 Hz), 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 (MgSO4)
  5. customevaporated
  6. customThe residue was purified by flash chromatography (silica gel, 35% EtOAc/isohexane)

出典と根拠

ORDレコード
ord-b0a1560958934dc68ff2f8cd9fa2cbad
出典データセット
uspto-grants-2005_08
特許番号
US06936608B2

関連ノート

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