Boron tribromide → HCID 136082626, compound
Reaction equation
[Cl:1][C:2]1[CH:31]=[CH:30][C:5]2[NH:6][C:7](=[O:29])[CH:8]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=3[Cl:28])[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17]C)=[C:13]([CH3:19])[CH:12]=3)[C:4]=2[CH:3]=1.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:31]=[CH:30][C:5]2[NH:6][C:7](=[O:29])[CH:8]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=3[Cl:28])[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([CH3:19])[CH:12]=3)[C:4]=2[CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
7-Chloro-3-(2-chloro-4-fluorobenzyl)-5-(4-methoxy-3-methylphenyl)-1H-benzo[e][1,4]diazepin-2(3H)-one (0.158 g, 0.345 mmol) was dissolved in dichloromethane (DCM, 2 mL) and BBr3 in DCM (1 M, 1.73 mL, 1.73 mmol) was added dropwise. The mixture was stirred at room temperature for 4 h. then quenched with methanol and diluted with ethyl acetate. The organic solution was washed with saturated sodium bicarbonate (aq) then brine. It was concentrated onto silica gel then chromatographed on silica gel eluting with 35-40-45% ethyl acetate in hexanes to give 7-chloro-3-(2-chloro-4-fluorobenzyl)-5-(4-hydroxy-3-methylphenyl)-1H-benzo[e][1,4]diazepin-2(3H)-one as a yellow oil which precipitated as a pale yellow solid from chloroform (158 mg, 0.345 mmol).