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

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).

1. temperatureThe reaction mixture was cooled to 0° C.
2. customquenched by the cautious addition of 1 M NaOH
3. additionThe reaction mixture was diluted with ether
4. washwashed with water twice
5. dry with materialbrine, dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was triturated with 10% ethyl acetate/hexanes (300 mL)

ORD record

ord-a4e07a48cd9a43d79923488e2496176b

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952180B2