N-[bis(dimethylamino)boranyl]-N-methylmethanamine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1-bromo-4-(trifluoromethoxy)benzene (2.41 g), tris(dimethylamino)borane (1.43 g), sodium t-butoxide (1.34 g), tris(dibenzylideneacetone)dipallidium (18 mg), and o-tolylphosphine (12 mg) in toluene (30 ml) was heated under reflux for 4 h. The mixture was cooled, diluted with water (30 mL) and extracted with ethyl acetate (3×10 mL). The combined organic fractions were washed with brine, dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by chromatography on silica gel, eluting with hexane/EtOAc (99:1 increasing to (95:5) to give the title compound as an oil (600 mg). 1H NMR (360 MHz, CDCl3) δ2.95 (6 H, s), 6.66 (2 H, d, J 9 Hz), and 7.08 (2 H, d, J 8.5 Hz). m/z (ES+) m/z 206 (M+1). was heated under reflux for 4 h The mixture was cooled extracted with ethyl acetate (3×10 mL) The combined organic fractions were washed with brine dried (MgSO4) the solvent was evaporated under reduced pressure The residue was purified by chromatography on silica gel eluting with hexane/EtOAc (99:1 increasing to (95:5)