2'-Fluoro-5'-nitrobiphenyl-2-carbonitrile → 5'-Amino-2'-fluorobiphenyl-2-carbonitrile

A cooled (0° C.) suspension of 2′-fluoro-5′-nitrobiphenyl-2-carbonitrile (24.2 g, 100 mmol) in EtOH (150 ml) and THF (150 ml) was treated with SnCl22H2O (67.7 g, 300 mmol) and the mixture was stirred to ambient temperature over 12 h. The solvent was removed in vacuo and the residue treated with ice-cold aqueous 2 N NaOH solution (750 ml). The resulting slurry was stirred for 60 min then extracted with CH2Cl2 (2×400 ml). The organics were combined, washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated to give a red solid. Crystallisation from toluene gave 5′-amino-2′-fluorobiphenyl-2-carbonitrile as a cream-coloured solid (16 g, 75%): δH (400 MHz, CDCl3 ) 3.65 (2H, br), 6.67-6.73 (2H, m), 7.00 (1H, t, J 9), 7.44-7.49 (2H, m), 7.64 (1H, td, J 9 and 2), 7.75 (1H, dd, J 8 and 2); m/z (ES+) 213 (100%, [MH]+).

1. temperatureA cooled
2. additionwas treated with SnCl22H2O (67.7 g, 300 mmol)
3. customThe solvent was removed in vacuo
4. additionthe residue treated with ice-cold aqueous 2 N NaOH solution (750 ml)
5. stirringThe resulting slurry was stirred for 60 min
6. extractionthen extracted with CH2Cl2 (2×400 ml)
7. washwashed with water, brine
8. dry with materialdried over anhydrous MgSO4
9. filtrationfiltered
10. concentrationconcentrated
11. customto give a red solid
12. customCrystallisation from toluene

ORD record

ord-df85d57c7b6b45859275b45e7f912a94

Source dataset

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07279580B2