4-(3,4-Dichlorophenyl)butanoic acid → 4-(3,4-Dichlorophenyl)butan-1-ol

Participants

Reaction Steps

At 0° C. to a solution of 4-(3,4-dichlorophenyl)butanoic acid (3.7 g, 16 mmol) in dry THF (50 mL) was added borane THF complex (31.7 mL, 1.00 M in THF, 31.7 mmol) cautiously over 15 min and the reaction mixture allowed to warm to rt overnight. The reaction mixture was cooled to 0° C. and quenched by the cautious addition of 1 M NaOH. The reaction mixture was diluted with ether, washed with water twice, then brine, dried over MgSO4, filtered and concentrated. The residue was triturated with 10% ethyl acetate/hexanes (300 mL) to give Intermediate 20A (3.50 g, 100%) as white powder. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.47-1.66 (4H, m), 2.53 (2H, t, J=7.5 Hz), 3.55-3.61 (2H, m), 6.94 (1H, dd, J=8.2, 2.1 Hz), 7.17-7.21 (1H, m), 7.26 (1H, d, J=8.3 Hz).

Provenance & Evidence