2-Bromo-1-fluoro-4-nitrobenzene → HCID 22285303, compound

Participants

Reaction Conditions

Reaction Steps

To a degassed solution of 2-bromo-1-fluoro-4-nitrobenzene (6.44 g, 29.3 mmol), 4-tri-n-butylstannylpyridine (14.0 g, 38.0 mmol), lithium chloride (12.4 g, 293 mmol) and copper(I) iodide (0.56 g, 2.93 mmol) in N,N-dimethylacetamide (40 mL) was added tetrakis(triphenylphosphine)palladium(0) (1.69 g, 1.46 mmol) and the reaction heated at 80° C. for 18 h. After cooling to ambient temperature the solvent was evaporated and the residue was diluted with dichloromethane (800 mL) and the mixture stirred vigorously for 30 min then filtered. The organics were washed with water (500 mL) and brine (300 mL), dried over anhydrous magnesium sulfate, filtered and evaporated to give a black oil. The residue was purified by silica gel chromatography eluting with iso-hexane (containing 1% methanol and 1% triethylamine) on a gradient of ethyl acetate (20-50%) to give 4-(2-fluoro-5-nitrophenyl)pyridine as an off-white solid (5.60 g, 88%): δH (360 MHz, CDCl3) 7.38 (1H, t, J 9), 7.50-7.53 (2H, m), 8.30-8.35 (1H, m), 8.41-8.44 (1H, m), 8.76-8.78 (2H, m).

Provenance & Evidence