Propargyl bromide → HCID 10796999, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 23.63 g (0.2 mol) of 4-aminobenzonitrile, 32.72 g (0.22 mol) of an 80% solution of 3-bromo-1-propyne in toluene, and 38.3 ml (0.22 mol) of N-ethyl-N-(1-methylethyl)-2-propanamine in 500 ml toluene is heated at 90° C. for eighteen hours. Ethyl acetate is added to the reaction suspension, and the suspension is washed three times with water. The organic layer is separated, dried (magnesium sulfate), and concentrated to give 32.5 g of a dark brown oil which crystallizes on standing. This is dissolved in a minimum amount of toluene and applied to a column of 1 kg of flash silica gel which is packed in toluene-ethyl acetate (20:1). Elution with the same solvent gives 24.66 g (78.9%) of the product as a cream colored solid; mp 68°-70° C.

Provenance & Evidence