Borane → 2-(2-Bromothiophen-3-yl)ethan-1-amine

2-(2-Bromothiophen-3-yl)acetonitrile (1.44 g, 7.13 mmol) was added slowly to a stirred solution of borane in THF (1.0 M, 15.7 mL, 15.7 mmol). The mixture was then heated to reflux for 14 h. The reaction mixture was allowed to cool to ambient temperature before residual borane was destroyed by careful dropwise addition of MeOH (10 mL). After the quench was complete, HCl gas was bubbled through the solution for 20 min and then the solvent was removed in vacuo. The residue was dissolved again in MeOH (20 mL) and concentrated twice more. The resulting white solid was dissolved in a biphasic mixture of dichloromethane and 1 N aqueous NaOH. The organic layer was separated, washed with brine, dried and concentrated to a colorless oil (1.34 g, 6.50 mmol, 92% yield). MS (M+H)+ 206/208.

1. temperatureThe mixture was then heated
2. temperatureto reflux for 14 h
3. customwas destroyed by careful dropwise addition of MeOH (10 mL)
4. customHCl gas was bubbled through the solution for 20 min
5. customthe solvent was removed in vacuo
6. dissolutionThe residue was dissolved again in MeOH (20 mL)
7. concentrationconcentrated twice more
8. dissolutionThe resulting white solid was dissolved in a biphasic mixture of dichloromethane and 1 N aqueous NaOH
9. customThe organic layer was separated
10. washwashed with brine
11. customdried

ORD record

ord-e0f25623a509484fbbffbcb311789907

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07858785B2