Hydrochloric Acid → 1-(3-Bromophenyl)ethanamine

A mixture of 3′-bromoacetophenone (2.66 mL, 20 mmol), ammonium formate (6.31 g, 100 mmol) and dichloro(pentamethylcyclopentadienyl)rhodium(III)dimer (124 mg, 0.2 mmol) in anhydrous methanol (20 mL) under an atmosphere of nitrogen was heated at reflux for 5 hours then allowed to cool to room temperature overnight. The mixture was diluted with water (20 mL), acidified to pH 2 with dilute aqueous hydrochloric acid (2M) and washed with dichloromethane (2×60 mL). The aqueous solution was basified to pH 12 with solid potassium hydroxide, extracted with dichloromethane (3×50 mL) and the extracts washed with brine (50 mL), dried (Na2SO4) and concentrated under reduced pressure to give 1-(3-bromophenyl)ethanamine (3.4 mg, 85%) as a yellow liquid.

1. temperaturewas heated
2. temperatureat reflux for 5 hours
3. washwashed with dichloromethane (2×60 mL)
4. extractionextracted with dichloromethane (3×50 mL)
5. washthe extracts washed with brine (50 mL)
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated under reduced pressure

ORD record

ord-a1bc84a6713c4ca5bcf2bc2206a26164

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09029386B2