2-Bromo-3-nitro-5-(trifluoromethyl)pyridine → 3-Nitro-5-(trifluoromethyl)picolinonitrile

Participants

Reaction Steps

2-Bromo-3-nitro-5-trifluoromethyl-pyridine (10.00 g, 36.87 mmol) was dissolved in toluene (250 ml) with stirring to give a pale yellow solution. Tetrabutylammonium bromide (11.90 g, 36.9 mmol) was added followed by copper(I) cyanide (9.92 g, 111 mmol) and the mixture was heated at reflux for 9 hrs. After cooling to RT, the reaction mixture was partitioned between water (750 ml) and EtOAc (750 ml). The organic fractions were combined, washed with water (2×250 ml) and brine (100 ml), dried dried (MgSO4) and concentrated in vacuo to afford the title product. 1H-NMR: [400 MHz, DMSO-d6 δH 9.55 (1H, m, ArH), 9.24 (1H, m, ArH)

Provenance & Evidence