Stannous chloride dihydrate → 2-Fluoro-2'-(methylthio)biphenyl-5-ylamine
Reaction equation
[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]=1Participants
Procedure
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).
Workup
- customThe solvent was evaporated
- stirringthe residue stirred with 2 N sodium hydroxide solution (240 ml) for 18 h
- extractionThe resulting suspension was extracted with dichloromethane (3×200 ml)
- dry with materialThe combined organic extracts were dried (MgSO4)
- customevaporated
- customThe residue was purified by flash chromatography (silica gel, 35% EtOAc/isohexane)
Sources & evidence
- ORD record
- ord-b0a1560958934dc68ff2f8cd9fa2cbad
- Source dataset
- uspto-grants-2005_08
- Patent number
- US06936608B2
Reaction notes
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