2-Methoxy-4-nitroaniline → Thiophene, 2-(2-methoxy-4-nitrophenyl)-

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 38.1 g (0.23 mole) of 2-methoxy-4-nitroaniline and 38.1 g (0.6 mole) of copper powder in 953.0 g (11.33 mole) of thiophene was heated at 55° C. During a 1.1 hour period 40.5 ml (0.34 mole) of t-butylnitrite was added to the warm reaction mixture. After complete addition the mixture was heated at 70° C. for approximately 18 hours then cooled to room temperature. The solvent was removed from the reaction mixture by distillation under reduced pressure to leave a residue. The residue was purified by column chromatography on silica gel, eluting with heptane:toluene (25:75), to yield 29.0 g of 2-(2-methoxy-4-nitrophenyl)thiophene.

Provenance & Evidence