Boron tribromide → 4-Bromo-3-nitrophenol
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8]C)=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].B(Br)(Br)Br>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 1-bromo-4-methoxy-2-nitrobenzene (2.32 g, 10 mmol) in 75 mL of dichloromethane at 0° C. was added BBr3 solution (1 M in DCM, 12 mL, 12 mmol) dropwise. The solution was allowed to warm to room temperature and stirred for 16 h. GC/MS showed starting material still left so another 12 mL of BBr3 solution was added and the reaction mixture refluxed for 4 h. The reaction mixture was cooled in ice and quenched with water. After washing successively with saturated NaHCO3(aq) and brine, the organic layer was dried over MgSO4, filtered and evaporated. The resulting yellow solid was flash chromatographed (25% EtOAc/hexane) to give 1.5 g of product in (69%) yield as a pale yellow solid: MS (EI) m/z 218 (M+).