Acetic Acid → HCID 961624, compound

Participants

Reaction Conditions

Reaction Steps

Benzylaniline (3.69 g, 34.8 mmol), AcOH (1.11 mL), and NaBH3CN were added to a solution of 3-chloro-4-fluoroaniline (5.07 g, 34.8 mmol) in MeOH (200 mL) containing molecular sieves. The resulting mixture was stirred at 23° C. for 18 h. Sieves were removed by filtration and the filtrate was concentrated. The residue was partitioned between saturated aqueous sodium bicarbonate solution (100 mL) and CH2Cl2 (50 mL, 2×20 mL). The combined organic extracts were dried over MgSO4 and concentrated. The residue was purified by flash column chromatography (SiO2, 0-12% EtOAc/hexanes gradient) to give N-benzyl-3-chloro 4-fluoroaniline (7-1) 1H NMR (300 MHz, CDCl3) δ 7.36-7.25 (m, 5H), 6.93 (dd, J=8.8, 5.8 Hz, 1H), 6.62 (dd, J=6.1, 3.1 Hz, 1H), 6.44 (ddd, J=8.9, 3.7, 3.1 Hz, 1H), 4.27 (s, 2H), 3.98 (brs, 1H).

Provenance & Evidence