Hydrochloric Acid → 3-(2,5-Difluorophenyl)prop-2-en-1-ol

Temperature

0 °C

A mixture of (2E)-3-(2,5-difluorophenyl)acrylic acid (1 g, 5.43 mmol) and N,N-diisopropylethylamine (1.7 mL, 9.8 mmol) in tetrahydrofuran (THF) was treated with isobutyl chloroformate (1.4 mL, 10.8 mmol) at room temperature. The reaction mixture was stirred for 30 minutes, and then filtered. The filtrate was cooled to 0° C. and 2M lithium borohydride (4.1 mL, 8.2 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 30 minutes then at room temperature for 30 minutes. Ice and 1N hydrochloric acid were added to the reaction mixture to adjust the pH to 7. The aqueous layer was extracted with ethyl acetate twice. The combined organic extracts were dried over sodium sulfate and concentrated to dryness under reduced pressure. Silica gel chromatography with hexanes/ethyl acetate (3:2) afforded desired product, 750 mg (82%).

1. filtrationfiltered
2. stirringThe reaction mixture was stirred at 0° C. for 30 minutes
3. waitat room temperature for 30 minutes
4. extractionThe aqueous layer was extracted with ethyl acetate twice
5. dry with materialThe combined organic extracts were dried over sodium sulfate
6. concentrationconcentrated to dryness under reduced pressure

ORD record

ord-ab0407af24284d939187799dfa50b16e

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07875715B2