Potassium Fluoride → HCID 86667306, compound

Participants

Reaction Steps

To a solution of 1-bromo-4-(nitromethyl)benzene (5.00 g, 20 mmol) in toluene (40 mL) was added palladium tetrakis(triphenylphosphine) (2.67 g, 2.31 mmol), 4-(trifluoromethyl)phenylboronic acid (5.28 g, 27.8 mmol) and potassium fluoride (4.0 g, 69 mmol). The reaction mixture was purged with nitrogen and heated to reflux. Water (10 mL) was added and the mixture was refluxed overnight. The mixture was diluted with saturated aqueous NH4Cl and the phases separated. The aqueous layer was extracted with ethyl acetate (20 mL*3). The combined organic layers were washed with water (50 mL*3), brine, dried over Na2SO4 and concentrated. The crude residue was purified by silica gel chromatography to give 4-(nitromethyl)-4′-(trifluoromethyl)biphenyl (2.0 g) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 7.75-7.66 (m, 6H), 7.57 (d, J=8.0 Hz, 2H), 5.51 (s, 2H).

Provenance & Evidence