3,5-Difluorobenzaldehyde → 1-(3,5-Difluorophenyl)ethan-1-ol

Temperature

2.5 °C

To a solution of 3,5-difluorobenzaldehyde (3.00 g, 21.1 mmol) in THF (30 mL) at 0-5° C. was added methylmagnesium bromide in THF (3.0 M; 8.44 mL, 25.3 mmol) dropwise. The mixture was stirred at 0-5° C. for 1 h, quenched with brine, and then extracted with EtOAc (2 times). The combined organic phases were washed with water and brine, dried over Na2SO4, and concentrated under reduced pressure to give the sub-title compound as a colorless oil (3.02 g, 90.4%). 1H NMR (300 MHz, CDCl3) δ 6.89 (m, 2H), 6.69 (m, 1H), 4.88 (q, J=6.3 Hz, 1H), 1.47 (d, J=6.3 Hz, 3H) ppm.

1. customquenched with brine
2. extractionextracted with EtOAc (2 times)
3. washThe combined organic phases were washed with water and brine
4. dry with materialdried over Na2SO4
5. concentrationconcentrated under reduced pressure

ORD record

ord-c2ce6807f25646139360e32f1208f318

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09200004B2