2-(2-bromophenoxy)acetonitrile → 2-(2-Bromophenoxy)ethan-1-amine

Temperature

0 °C

Into a 500-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 2-(2-bromophenoxy)acetonitrile (5.63 g, 26.68 mmol, 1.00 equiv) in tetrahydrofuran (20 mL). This was followed by the addition of BH3 in tetrahydrofuran (143 mL, 5.30 equiv) dropwise with stirring at 0° C. The resulting solution was stirred overnight at 20° C. in an oil bath and quenched by the addition of water (10 ml). The resulting mixture was concentrated under vacuum and diluted with water. The pH value of the aqueous solution was adjusted to 10 with 1N sodium hydroxide and extracted with 6×50 mL of dichloromethane. The organic layers was combined and concentrated under vacuum. This resulted in 5.67 g (crude) of 2-(2-bromophenoxy)ethanamine as pale brown oil.

1. customInto a 500-mL 3-necked round-bottom flask purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. stirringThe resulting solution was stirred overnight at 20° C. in an oil bath
4. customquenched by the addition of water (10 ml)
5. concentrationThe resulting mixture was concentrated under vacuum
6. additiondiluted with water
7. extractionextracted with 6×50 mL of dichloromethane
8. concentrationconcentrated under vacuum
9. customThis resulted in 5.67 g (crude) of 2-(2-bromophenoxy)ethanamine as pale brown oil

ORD record

ord-17fb56389d834e278caade34d226d826

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193693B2