Sodium Carbonate → 1-(3-Methoxyphenyl)-2-methyl-4-nitrobenzene

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Reaction Steps

A solution of 2-bromo-5-nitrotoluene (40.0 gm, 185 mmol) in 1,2-dimethoxyethane (600 mL) was added to tetrakis(triphenylphosphine)palladium(0) (9.77 gm, 9.25 mmol) under nitrogen at room temperature. A solution of 3-methoxyphenylboronic acid (31.5 gm, 207 mmol) in ethanol (150 mL) was added. Finally, 2M aqueous sodium carbonate (800 mL) was added and the mixture was heated under reflux with rapid mechanical stirring for 18 h. After being cooled, the mixture was partitioned between ethyl acetate and water and the organic phase was dried (Na2SO4) and concentrated under reduced pressure. Purification by column chromatography on silica gel eluting with hexane:ethyl acetate=98:2 then 95:5 gave 1-(3-methoxyphenyl)-2-methyl-4-nitrobenzene (40.55 gm, 90%).

Provenance & Evidence