Bromobenzene → HCID 13837941, compound

Participants

Reaction Steps

A mixture of 60.0 g (0.32 mole) of 5-methoxy-1H-indole-2-carboxylic acid, 35.0 ml (52.2 g; 0.32 mole) of bromobenzene, 36.0 g (0.64 mole) of potassium hydroxide, and 10.0 g (0.13 mole) of copper (II) oxide in 750 ml of N,N-dimethylformamide was stirred and heated at reflux under a nitrogen atmosphere for six hours. The cooled reaction mixture was added to 1.5 kg of ice/water and filtered through a bed of Celite filter-aid. Acidification of the filtrate with dilute hydrochloric acid precipitated the product. The solid was filtered and washed with water to yield 83.0 g (95% yield) of crude acid product. A sample recrystallized from ether/hexane was analytically pure, mp 197°-204° C.

Provenance & Evidence