Sulfuric Acid → Methyl (4-bromo-2-fluorophenyl)acetate

Temperature

80 °C

A solution of a crude (72% purity) mixture of 2-(4-bromo-2-fluorophenyl)acetonitrile and 2-(4-bromo-2-fluorophenyl)acetamide (1.4:1 ratio, 2.0 g) in methanol (6 mL) was treated dropwise with conc. sulfuric acid (4 mL, 75 mmol). The vessel was then sealed, heated in an oil bath at 80° C., and stirred for three days. At this point the reaction was cooled to room temperature and was diluted slowly with water (50 mL). The mixture was then extracted twice with dichloromethane. The organic layers were combined and washed with saturated aq sodium bicarbonate and brine. The organic solution was dried over sodium sulfate, filtered and concentrated in vacuo to afford the crude title compound as a clear oil. The crude oil was used directly in the next reaction. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.63 (s, 3 H) 3.74 (s, 2 H) 7.34 (t, J=8.08 Hz, 1 H) 7.38-7.43 (m, 1 H) 7.55 (dd, J=9.60, 2.02 Hz, 1 H).

1. customThe vessel was then sealed
2. temperatureAt this point the reaction was cooled to room temperature
3. extractionThe mixture was then extracted twice with dichloromethane
4. washwashed with saturated aq sodium bicarbonate and brine
5. dry with materialThe organic solution was dried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo

ORD record

ord-de0c3b78b8f7427b86cb981952bb7885

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09084794B2