Benzene → 4-Nitro-1,1'-biphenyl

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-nitro-aniline (3.77 g; 0.0273 mole), trichloroacetic acid (6 g; 0.0367 mole), cuprous chloride (0.14 g; 0.0014 mole) and trimethylorthoformate (5.8 g; 0.0548 mole) in benzene (140.6 g; 1.8 mole) was heated to 60° C. Aliquots of sodium nitrite (2.3 g; 0.0333 mole) were added to the thus obtained mixture. The mixture was maintained under stirring for 22 hours at 60° C. and then hydrolyzed with water and diluted hydrochloric acid. The organic layer was separated, washed with water and concentrated. Crystallization of the residue from methanol afforded 5.8 g of 4-nitro-biphenyl, melting at 114°-116° C. Yield, 80%.

Provenance & Evidence