Acetic Anhydride → 5-Bromo-2-methoxybenzonitrile

Temperature

100 °C

A mixture of 5-Bromo-o-anisaldehyde (6.45 g), hydroxylamine hydrochloride (2.2 g), sodium acetate (4.1 g) and acetic acid (20 mL) was heated at 100° C. with stirring for 1 h. Acetic anhydride was added (20 mL) and the mixture was refluxed for 8 h. The reaction mixture was poured onto ice water and the mixture was made basic by the careful addition of 50% sodium hydroxide. The product was extracted with ether, the ether extracts were dried over magnesium sulfate and the sovent was removed in vacuo. The residue was crystallized from ether/hexane to afford 5-Bromo-2-methoxybenzonitrile.

1. temperaturethe mixture was refluxed for 8 h
2. additionThe reaction mixture was poured onto ice water
3. extractionThe product was extracted with ether
4. dry with materialthe ether extracts were dried over magnesium sulfate
5. customthe sovent was removed in vacuo
6. customThe residue was crystallized from ether/hexane

ORD record

ord-08c104c8edfe495985533ecb2240fa53

Source dataset

uspto-grants-1995_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05428164