2-Bromobenzyl cyanide → 2-Bromophenethylamine

Temperature

0 °C

Into a 500-mL 3-necked round-bottom flask, was placed 2-(2-bromophenyl)acetonitrile (9.8 g, 49.99 mmol, 1.00 equiv), tetrahydrofuran (50 mL). This was followed by the addition of BH3 solution (250 mL, 1N in tetrahydrofuran) dropwise with stirring at 0° C. The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of 50 mL of water. The resulting mixture was concentrated under vacuum. The resulting solution was diluted with 50 mL of H2O. The pH value of the aqueous solution was adjusted to 2 with aq. hydrogen chloride (5 N). The aqueous solution was washed with 3×20 mL of EA and adjusted to pH to 11 with sodium hydroxide. The resulting aqueous solution was extracted with 3×50 mL of ethyl acetate and the organic layers combined and concentrated under vacuum. This resulted in 5 g (50%) of 2-(2-bromophenyl)ethanamine as brown oil.

1. customInto a 500-mL 3-necked round-bottom flask, was placed
2. stirringThe resulting solution was stirred overnight at room temperature
3. customThe reaction was then quenched by the addition of 50 mL of water
4. concentrationThe resulting mixture was concentrated under vacuum
5. additionThe resulting solution was diluted with 50 mL of H2O
6. washThe aqueous solution was washed with 3×20 mL of EA
7. extractionThe resulting aqueous solution was extracted with 3×50 mL of ethyl acetate
8. concentrationconcentrated under vacuum
9. customThis resulted in 5 g (50%) of 2-(2-bromophenyl)ethanamine as brown oil

ORD record

ord-5766054f67004732b8c33316b45d5430

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916560B2