Diisobutylaluminumhydride → 3-(4-Chloro-3-fluorophenyl)prop-2-en-1-ol

Temperature

-78 °C

(E)-Ethyl 3-(4-chloro-3-fluorophenyl)acrylate (18.3 g, 80.0 mmol) was combined with toluene (200 mL) and cooled to −78° C. Diisobutylaluminium hydride (“DIBAL-H”) (100 g, 176 mmol) (25% in toluene) was then added over one hour. The reaction was then allowed to agitate and warm up to ambient temperature over 2 hours. After agitating for an additional hour, the reaction was quenched with ice (200 g), and 6M HCl (100 mL) was added slowly. The aqueous layer was separated and extracted once with ethyl acetate. The combined organics were washed with brine, dried and evaporated to give a waxy solid, which was triturated with hexanes to give (E)-3-(4-chloro-3-fluorophenyl)prop-2-en-1-ol (14.0 g, 75.0 mmol, 93.7% yield) as a solid.

1. temperaturewarm up to ambient temperature over 2 hours
2. stirringAfter agitating for an additional hour
3. customthe reaction was quenched with ice (200 g), and 6M HCl (100 mL)
4. additionwas added slowly
5. customThe aqueous layer was separated
6. extractionextracted once with ethyl acetate
7. washThe combined organics were washed with brine
8. customdried
9. customevaporated
10. customto give a waxy solid, which
11. customwas triturated with hexanes

ORD record

ord-a6bcb729f7b34eb1bcc2a43e0bd35d80

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697715B2