Boron tribromide → 3-Ethyl-3-(3-hydroxy-phenyl)-azepan-2-one
Reaction equation
B(Br)(Br)Br.[CH2:5]([C:7]1([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21]C)[CH:16]=2)[CH2:13][CH2:12][CH2:11][CH2:10][NH:9][C:8]1=[O:14])[CH3:6]>C(Cl)Cl>[CH2:5]([C:7]1([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=2)[CH2:13][CH2:12][CH2:11][CH2:10][NH:9][C:8]1=[O:14])[CH3:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A 1M solution of BBr3 (7.1 mL, 7.1 mmol) in CH2Cl2 was added to 3-ethyl-3-(3-methoxy-phenyl)-azepan-2-one (as described in Step A above) (0.800 g, 0.323 mmol) dissolved in anhydrous CH2Cl2 (5 mL) at −78° C. After 48 h of stirring at room temperature, the reaction was quenched with H2O, extracted with CH2Cl2 (3×), dried (MgSO4), concentrated and purified using reverse phase chromatography (95/5-5/95 H2O/CH3CN with 0.1% TFA, flow=65 mL/min) to give the title compound.