Ammonia → 3-Bromo-4-methylbenzonitrile

Participants

Reaction Steps

3-Bromo-4-methyl-benzoic acid (3 g) in toluene (75 ml) was treated with oxalyl chloride (10 ml) and DMF (4 drops). The mixture was then stirred at 20 C for 3 h. and then the solvent evaporated giving a yellow solid. This in turn was dissolved in THF (30 ml) containing N-methyl-morpholine (1.5 ml). Aqueous ammonia (0.880, 40 ml) was then added and the mixture stirred for 18 h. The THF was then evaporated and the resulting amide intermediate collected by filtration as a colourless solid (2.9 g). This material was then suspended in thionyl chloride (35 ml) and was heated to 85 C for 6 h. The excess reagent was then evaporated and the residue purified on silica gel. Elution with 5-50% ethyl acetate in hexane gave the title compound as a white solid (1.4 g)

Provenance & Evidence