Bromine → 4-Bromo-2-fluoroanisole

To a flask containing 50 ml of chloroform was added 12.6 g of 2-fluoroanisole, and 16.0 g of bromine was added dropwise over 1 hour at 0° to 10° C. The mixture was stirred at the same temperature for 1 hour, and refluxed at 60° to 63° C. for 6 hours. After the reaction, the chloroform solution was washed with an aqueous solution of sodium hydrogen sulfite, an aqueous solution of sodium bicarbonate, and water, and dried over anhydrous sodium sulfate. The chloroform was evaporated to give 20.1 g of a crude product. The crude product was distilled under reduced pressure to give 16.2 g (yield 79%) of 4-bromo-2-fluoroanisole (95°-96° C./12 mmHg).

1. additionwas added dropwise over 1 hour at 0° to 10° C
2. temperaturerefluxed at 60° to 63° C. for 6 hours
3. customAfter the reaction
4. washthe chloroform solution was washed with an aqueous solution of sodium hydrogen sulfite
5. dry with materialan aqueous solution of sodium bicarbonate, and water, and dried over anhydrous sodium sulfate
6. customThe chloroform was evaporated
7. customto give 20.1 g of a crude product
8. distillationThe crude product was distilled under reduced pressure

ORD record

ord-b843a2ee38e14d31af154eb922733483

Source dataset

uspto-grants-1990_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04911862