3-Bromo-2,4,6-trimethylnitrobenzene → Benzene, 2-methoxy-1,3,5-trimethyl-4-nitro-

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-bromo-4-nitro-1,3,5-trimethylbenzene (2.0 g, 8.19 mmol) in methanol (20 mL) and pyridine (1.0 mL) under nitrogen was added sodium methoxide (6.2 mL, 32.8 mmol, 30% in methanol), and cuprous chloride (1.62 g, 16.4 mmol). The reaction mixture was heated to 85° C. After 16 hours, it was allowed to cool to room temperature. The solvent was removed under reduced pressure. The residue was extracted with ethyl acetate (2×80 mL). The organic phases were combined and washed with saturated aqueous NaCl (2×) and dried over magnesium sulfate. The solvent was removed under reduced pressure to give 3-nitro-2,4,6-trimethyl-1-methoxybenzene (0.86 g, 54%) was obtained as a light-yellow liquid.

Provenance & Evidence