3,5-Difluoro-2-methoxyphenylacetic acid → 2-(3,5-Difluoro-2-methoxyphenyl)ethan-1-ol

Temperature

60 °C

To a solution of 2-(3,5-difluoro-2-methoxyphenyl)acetic acid (1 g, 4.95 mmol) in THF (20 mL) at 0° C. was added 1M LAH (9.89 mL, 9.89 mmol) in THF and the resulting mixture was heated at 60° C. for 3 h. Mixture was then cooled and quenched with dropwise addition of water (0.5 mL), 1N NaOH (0.5 mL), and then 1 mL H2O. After stirring for 15 min. the mixture was filtered through celite. The filtrate was concentrated in vacuo. The residue was dried under high vacuum to afford 2-(3,5-difluoro-2-methoxyphenyl)ethanol (700 mg, 3.72 mmol, 75% yield) as a clear viscous oil. Used as is in the next step without further purification. 1H NMR (500 MHz, CDCl3) δ 6.83-6.72 (m, 2H), 3.90 (s, 3H), 3.87 (q, J=5.7 Hz, 2H), 2.92 (t, J=6.5 Hz, 2H), 1.73-1.64 (m, 1H).

1. temperatureMixture was then cooled
2. customquenched with dropwise addition of water (0.5 mL), 1N NaOH (0.5 mL)
3. filtrationwas filtered through celite
4. concentrationThe filtrate was concentrated in vacuo
5. customThe residue was dried under high vacuum

ORD record

ord-dcfa28f8d2a94b1b9e22af67ffa304fe

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09273067B2