Benzyl Bromide → 2-(Benzyloxy)-1-methoxy-4-nitrobenzene

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[OH:18].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[CH2:19]([O:18][C:10]1[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:9]=1[O:8][CH3:7])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Procedure

Potassium carbonate (1.65 gm; 12 mmol) was added to a solution of 2-methoxy-5-nitro phenol (1.69 g; 10 mmol) and benzyl bromide (1.71 gm; 10 mmol) in acetone (60 ml). The reaction mixture was refluxed for 12 hours. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate (150 ml) and water (50 ml). The ethyl acetate layer was separated, washed with water (2×50 ml), dried over anhydrous magnesium sulfate. Removal of the solvent under reduced pressure provided 2.5 g of 1-Benzyloxy-2-methoxy-5-nitrobenzene (Yield=96.5%)