Toluene → N-(p-Bromobenzyl)-N-(4-methoxyphenyl)hydrazine hydrochloride

Participants

Reaction Conditions

Reaction Steps

4-Methoxyphenyl hydrazine hydrochloride (1.0 eq) was added to a reaction flask containing of toluene (16 eq.; V/W of starting material) under nitrogen. To this reaction flask was added 4-bromo-benzylbromide (1.05 eq) and Et3N (2.1 eq). The reaction mixture was heated to about 100-105° C. and stirred for about 3 hours after which the reaction flask was cooled to room temperature. Ethyl acetate (10.0-fold, V/W of starting material) was added to the reaction flask and agitated for about 1.5 hours. The reaction mixture was filtered to collect the solid which was subsequently washed with toluene and dried in vacuo. Ethyl acetate was then added and the solution was agitated. The pH of the mixture was adjusted to a pH of 2 with saturated HO/Ethyl acetate solution and further agitated for 1 hour. The solid was then collected and washed with ethyl acetate and then air dried. The product was taken on to the next step without further purification.

Provenance & Evidence