1-Bromopropane → HCID 14500637, compound

Participants

Reaction Steps

50% Sodium hydride 4 g (160 mmol) in mineral oil was suspended, under nitrogen atmosphere, in 250 ml of anhydrous dimethylformamide. A solution of 15 g (69 mmol) of 2-(3-nitrobenzoyl)pyrrole, prepared, for example, as described in Preparation 3A, in 50 ml of anhydrous dimethylformamide was added thereto, at room temperature, in a dropwise fashion and under stirring. The resulting mixture was stirred for 12 additional hours and then a solution of 18 ml (197 mmol) of 1-bromopropane in 50 ml of dry dimethylformamide was added. The reaction mixture was stirred for 18 hours further and thereafter poured into 1000 ml of ethyl acetate, washed with water (5×500 ml), dried and evaporated in vacuo. Purification of the residue by column chromatography on 500 g of silica gel, using hexane-ethyl acetate (90:10) as eluant provided 17.61 g (98%) of 1-propyl-2-(3'-nitrobenzoyl)pyrrole, the title compound, as an oil.

Provenance & Evidence