Imidazole → {4-Chloro-2-[alpha-(1-imidazolyl)-benzyl]-phenyl}-(2,4-dichlorobenzyl)-ether

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Reaction Steps

23 g. of 5-chloro-2-hydroxybenzophenone is reduced with an excess of sodium borohydride in methanol, thus obtaining 10.5 g. of 5-chloro-2-hydroxybenzohydrol, m.p. 132°-134° (from benzene). 2.3 g. of this product is heated with 670 mg. of imidazole for 2.5 hours to 200°. The reaction mixture is then dissolved in ethanol, a small amount of water is added, and this yields 500 mg. of 4-chloro-2-[α-(1-imidazolyl)-benzyl]-phenol, m.p. 228°-232°. The product is stirred in 7.5 ml. of dimethylformamide with 65 mg. of sodium hydride suspension (80%) for 1.5 hours at room temperature and then combined with 440 mg. of 2,4-dichlorobenzyl chloride. After the mixture has been worked up as set forth in Example 1, it is recrystallized from benzene/cyclohexane, thus obtaining 430 mg. of {4-chloro-2-[α-(1-imidazolyl)-benzyl[-phenyl}-(2,4-dichlorobenzyl)-ether, m.p. 115°-120°.

Provenance & Evidence