Boron tribromide → 4-[1-(4-Bromophenyl)-2-(methylamino)ethyl]phenol

反応式

B(Br)(Br)Br.[Br:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([C:16]2[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=2)[CH2:13][NH:14][CH3:15])=[CH:8][CH:7]=1>ClCCl.C([O-])(O)=O.[Na+]>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([C:16]2[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=2)[CH2:13][NH:14][CH3:15])=[CH:8][CH:7]=1

参加物

実験手順

Boron tribromide (7.8 ml, 1.0M in dichloromethane) was added slowly to a solution of [2-(4-Bromo-phenyl)-2-(4-methoxy-phenyl)-ethyl]-methyl-amine (500 mg, 1.56 mmol) in dichloromethane (8 ml) at 0° C., under an atmosphere of nitrogen. The reaction mixture was allowed to warm to room temperature and then stirred for a further hour. The mixture was poured on to ice and then diluted with dichloromethane and saturated NaHCO3 solution. The organic layer was dried (MgSO4), filtered and concentrated to afford the desired product. LC/MS: (PS-B3) Rt 2.76 [M+H]+306.