Hydrochloric Acid → (4-Bromo-3-methylphenyl)methanamine

Borane in THF (25.5 ml) was added dropwise, at 0° C., under nitrogen to a solution of 4-bromo-3-methylbenzonitrile (1.0 g) in THF (dry, 20 ml). The solution was left at 0° C. for 30 min and then stirred at room temperature overnight. Methanol was added carefully to quench the reaction. Hydrochloric acid (2N, 20 ml) was added and the solution stirred at room temperature for 4 h. Further 2N hydrochloric acid (20 ml) was added and the mixture heated to reflux for several hours. Sodium bicarbonate was added to the cooled mixture till basic and extracted with dichloromethane (4×50 ml), dried and slowly evaporated to give an orange/yellow oil. This was then applied in methanol to a flash column of silica gel which was eluted with hexane: ethyl acetate (1:1)→ethyl acetate:methanol:0.88 ammonia (790:200:10) to give the title compound as a yellow/orange oil (364 mg).

1. customto quench
2. customthe reaction
3. stirringthe solution stirred at room temperature for 4 h
4. temperaturethe mixture heated
5. temperatureto reflux for several hours
6. extractionextracted with dichloromethane (4×50 ml)
7. customdried
8. customslowly evaporated
9. customto give an orange/yellow oil
10. washwas eluted with hexane: ethyl acetate (1:1)→ethyl acetate

ORD record

ord-f05e3cdc0a994c838c1b3a558abc467d

Source dataset

uspto-grants-1994_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05356893