Boron tribromide → 3-[[2-Fluoro-5-(3-fluorophenyl)phenyl]methylamino]phenol
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[CH:4][C:3]=1[CH2:15][NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23]C)[CH:18]=1.B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[CH:4][C:3]=1[CH2:15][NH:16][C:17]1[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=1Participants
4
Procedure
To a solution of N-[[2-fluoro-5-(3-fluorophenyl)phenyl]methyl]-3-methoxy-aniline (512 mg, 1.60 mmol, 1.0 eq) in CH2Cl2 (10 mL) at −70° C. was added BBr3 (0.6 mL, 65.3 mmol, 40.8 eq). The reaction was warmed to room temperature and stirred for 1 h. The reaction was then cooled to 0° C. and quenched by addition of water. The pH of the solution was adjusted to pH 7 with aqueous Na2CO3, then extracted with EtOAc. The organic extract was washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo to give the title compound as a colourless oil (460 mg, 94%).