Phosphorus tribromide → Methyl 2-(2-(2-Propyl)-4-Bromomethyl-Phenoxy)-2-(3-Chlorophenyl)Acetate
Reaction equation
[CH3:1][CH:2]([C:4]1[CH:22]=[C:21]([CH2:23]O)[CH:20]=[CH:19][C:5]=1[O:6][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=1)[C:8]([O:10][CH3:11])=[O:9])[CH3:3].P(Br)(Br)[Br:26]>C(Cl)(Cl)(Cl)Cl>[CH3:1][CH:2]([C:4]1[CH:22]=[C:21]([CH2:23][Br:26])[CH:20]=[CH:19][C:5]=1[O:6][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=1)[C:8]([O:10][CH3:11])=[O:9])[CH3:3]Participants
4
Procedure
To a solution of 0.110 g (0.31 mmol) of the product of Step A dissolved in 1.0 mL of carbon tetrachloride was added 0.03 mL (1.6 mmol) of phosphorous tribromide and the reaction mixture was stirred at room temperature for 10 minutes. Carbon tetrachloride was evaporated from the reaction mixture several times to remove the hydrogen bromide, then the residue was purified on a silica gel flash chromatography column eluted with 15% EtOAc-hexane. The purified fractions were evaporated in vacuo affording 0.104 g (80%) of the title compound.