Pyridine → 4-Bromo-2,6-difluorophenethyl acetate

A solution of 2-(4-bromo-2,6-difluorophenyl)ethanol (1.392 mmol) in dichloromethane (2 mL) was treated with pyridine (4.00 mL), acetic anhydride (4.18 mmol), and 4-(dimethylamino)pyridine (0.070 mmol). The reaction was stirred at room temperature for three days. At this point, the reaction contents were concentrated to in vacuo to minimum volume. The material was diluted with water (50 mL) and was extracted twice with ethyl acetate. The combined organic layers were washed with saturated aq sodium bicarbonate, twice with brine, dried over sodium sulfate, filtered and concentrated in vacuo to afford the title compound as a beige oil (330 mg, 76% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.95 (s, 3 H) 2.91 (t, J=6.32 Hz, 2 H) 4.18 (t, J=6.44 Hz, 2 H) 7.47 (d, J=7.07 Hz, 2 H).

1. customAt this point, the reaction contents
2. concentrationwere concentrated to in vacuo to minimum volume
3. additionThe material was diluted with water (50 mL)
4. extractionwas extracted twice with ethyl acetate
5. washThe combined organic layers were washed with saturated aq sodium bicarbonate, twice with brine
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-a0718a7094f84735b5936dcc8acf17aa

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09084794B2