Stannous chloride dihydrate → 5'-Amino-2'-fluorobiphenyl-2-carbonitrile

To a stirred suspension of 2′-fluoro-5′-nitrobiphenyl-2-carbonitrile (18.71 g, 77.2 mmol) in THF (150 ml) and ethanol (150 ml) was added tin(II) chloride dihydrate (52.42 g, 232.4 mmol) and the mixture was stirred at room temperature for 22.5 h. The mixture was evaporated in vacuo and the residue was treated with ice-cold 2 N aqueous NaOH (800 ml). The resulting mixture was stirred for 1.5 h, then extracted with dichloromethane (2×800 ml). The combined organic extracts were washed with saturated aqueous NaCl (200 ml), dried (MgSO4), and evaporated in vacuo. The residue was recrystallised from hot toluene (100 ml) to afford 11.33 g (69%) of 5′-amino-2′-fluorobiphenyl-2-carbonitrile as a white solid: 1H NMR (360 MHz, CDCl3) δ 3.65 (2H, br s), 6.67-6.73 (2H, m), 7.00 (1H, t, J 9.0 Hz), 7.46 (1H, td, J 7.6, 1.1 Hz), 7.49 (1H, d, J 7.4 Hz), 7.64 (1H, td, J 7.7, 1.3 Hz), 7.76 (1H, dd, J 7.7, 0.7 Hz).

1. customThe mixture was evaporated in vacuo
2. additionthe residue was treated with ice-cold 2 N aqueous NaOH (800 ml)
3. stirringThe resulting mixture was stirred for 1.5 h
4. extractionextracted with dichloromethane (2×800 ml)
5. washThe combined organic extracts were washed with saturated aqueous NaCl (200 ml)
6. dry with materialdried (MgSO4)
7. customevaporated in vacuo
8. customThe residue was recrystallised from hot toluene (100 ml)

ORD record

ord-52d3ac3165814f71933d945924fe5af4

Source dataset

uspto-grants-2005_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06936608B2