Hydrochloric Acid → 4-Chloro-2-(1H-imidazol-1-yl)phenol

Participants

Reaction Steps

1.1 g. of the 1-(2-methoxy-5-nitrophenyl)-imidazole obtained in Example 65 is reduced by heating for 5 minutes with 3.75 g. of tin(II) chloride in 20 ml. of concentrated hydrochloric acid. The thus-formed 3-(1-imidazolyl)-4-methoxyaniline (830 mg.) is converted according to Sandmeyer in the usual way into the 1-(5-chloro-2-methoxyphenyl)-imidazole (610 mg.; m.p. 52°-57°). After ether cleavage according to the literature citation in Example 56, 4-chloro-2-(1-imidazolyl)-phenol is obtained (425 mg.), which is etherified analogously to Example 58 with the use of 4 25 mg. of 2,4-dichlorobenzyl chloride.

Provenance & Evidence