Boron tribromide → Ethyl 3-(bromomethyl)phenoxyacetate
Reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([O:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)[Br:17]>ClCCl>[Br:17][CH2:2][C:3]1[CH:4]=[C:5]([O:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:7][CH:8]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-hydroxymethyl-1-ethoxycarbonylmethoxybenzene (1 g) in dichloromethane (10 ml) was added BBr3 (0.45 ml). After 1 hour, the solvent was evaporated in vacuo and the residue was dissolved in ethyl acetate. The organic layer was washed with NaHCO3 and brine. The dried solvent was evaporated in vacuo to give 3-bromomethyl-1-ethoxycarbonylmethoxybenzene (0.76 g). NMR (CDCl3, δ): 1.29 (3H, t, J=7 Hz), 4.24 (2H, d, J=7 Hz), 4.61 (2H, s), 5.00 (1H, d, J=3.0 Hz), 5.05 (1H, d, J=3.0 Hz), 6.7-7.1 (3H, m), 7.2-7.3 (1H, m)