3-(3,4-Dichlorophenyl)propionic acid → 3-(3,4-Dichlorophenyl)propan-1-ol

Temperature

0 °C

At rt to a suspension of 3-(3,4-dichlorophenyl)propanoic acid (2.0 g, 9.1 mmol) in THF (40 mL) was added borane-THF (18.3 mL, 1.00M in THF, 18.3 mmol). After 12 h, the reaction mixture was cooled to 0° C. and quenched by the cautious addition of 1M NaOH. The reaction mixture was diluted with ether, washed with water twice, then brine, and the organic portion dried over MgSO4, filtered, and concentrated. Trituration with 10% Ethyl acetate/Hexane (300 mL) gave a white powder which was collected by filtration to give Intermediate 17A (2.00 g, 9.80 mmol, 100% crude). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.73-1.81 (2H, m), 2.56-2.65 (2H, m), 3.59 (2H, t, J=6.4 Hz), 6.96 (1H, dd, J=8.0, 2.0 Hz), 7.22 (1H, d, J=2.0 Hz), 7.27 (1H, d, J=8.3 Hz).

1. customquenched by the cautious addition of 1M NaOH
2. additionThe reaction mixture was diluted with ether
3. washwashed with water twice
4. dry with materialbrine, and the organic portion dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. customTrituration with 10% Ethyl acetate/Hexane (300 mL) gave a white powder which
8. filtrationwas collected by filtration

ORD record

ord-915258dcd3a24caba6b510d3ca310d8c

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952180B2