Borane → 2-(2-Bromophenyl)-2-methylpropan-1-amine(WXG01973)

The derivative 2-(2'-bromophenyl)-2-methylpropionitrile from Example 1/A (2.24 g; 10 mmole) was dissolved in THF (25 ml) in an inert atmosphere. A solution of borane BH3 in THF (1 M; 25 ml; 25 mmole) was slowly added to the reaction medium. The new solution obtained was refluxed for 3 h. After cooling to room temperature, an aqueous solution of trifluoroacetic acid (50 ml; 1/1) was added dropwise to the reaction mixture. The mixture was refluxed for 1 h, then the solvents were evaporated off under reduced pressure. The residue was taken up in 60 ml of hydrochloric acid HCl (10%) and washed with 3×100 ml of ethyl acetate. The aqueous phase was alkalinised (12<pH<14) then extracted with 3×50 ml of dichloromethane. The organic phases were combined, washed with 2×100 ml of a saturated NaCl solution, dried over MgSO4 then filtered. The solvent was evaporated off under reduced pressure. The desired compound was obtained as a yellowish oil.

1. customThe new solution obtained
2. temperaturewas refluxed for 3 h
3. temperatureThe mixture was refluxed for 1 h
4. customthe solvents were evaporated off under reduced pressure
5. washwashed with 3×100 ml of ethyl acetate
6. extractionthen extracted with 3×50 ml of dichloromethane
7. washwashed with 2×100 ml of a saturated NaCl solution
8. dry with materialdried over MgSO4
9. filtrationthen filtered
10. customThe solvent was evaporated off under reduced pressure

ORD record

ord-294f5239ba9d45288336599aaa9e7c4e

Source dataset

uspto-grants-2000_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06093532