Hydrochloric Acid → 3-Bromo-N-(4-fluorophenyl)propanamide

5.75 ml of 4-fluoroaniline (6.65 g, 59.88 mmol, 1 equivalent) were initially charged in 65 ml of THF, 33 ml of 2 M trimethylaluminium solution in hexane (65.87 mmol, 1.1 equivalents) were added at −78° C. and the mixture was stirred for 20 min, slowly warming to RT. At −20° C., this solution was added dropwise to a solution of 6.54 ml (10 g, 59.8 mmol, 1 equivalent) of methyl 3-bromopropanoate in 65 ml of THF and then stirred at RT for 3 h. At 0° C., the reaction solution was acidified carefully with 1 N aqueous hydrochloric acid solution and extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered and concentrated. This gave 12.6 g (67% of theory; purity 78%) of the title compound which was reacted further without purification.

1. stirringstirred at RT for 3 h
2. customAt 0° C.
3. extractionextracted twice with ethyl acetate
4. dry with materialThe combined organic phases were dried over sodium sulphate
5. filtrationfiltered
6. concentrationconcentrated
7. customThis gave 12.6 g (67% of theory; purity 78%) of the title compound which was reacted further without purification

ORD record

ord-a9c175de9740434fa64511d5323b73ed

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09126998B2