Phosphorus tribromide → Methyl 3-(1-bromoethyl)benzoate
Reaction equation
O[CH:2]([C:4]1[CH:5]=[C:6]([C:10]([O:12][CH3:13])=[O:11])[CH:7]=[CH:8][CH:9]=1)[CH3:3].P(Br)(Br)[Br:15]>C1(C)C=CC=CC=1>[Br:15][CH:2]([C:4]1[CH:5]=[C:6]([C:10]([O:12][CH3:13])=[O:11])[CH:7]=[CH:8][CH:9]=1)[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
5 g (27.75 mmol) of methyl 3-(1-hydroxyethyl)benzenecarboxylate (Example 60A) were initially charged in 100 ml of toluene. At 0° C., 0.98 g (36.07 mmol) of phosphorus tribromide were added dropwise, and the mixture was stirred at RT for 45 min. The reaction solution was poured onto ice-water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and evaporated. The residue was purified by column chromatography on silica gel 60 (mobile phase:cyclohexane:ethyl acetate 50:1→40:1).