HCID 58960010, compound → HCID 44435668, compound

Participants

Reaction Steps

The title compounds were prepared as an inseparable mixture by methods analogous to those described in Example 5 as a result of performing a Grignard reaction with a 1:1.4 mixture of 2-bromomethyl-4,6-dimethylbenzonitrile and 4-bromomethyl-2,6-dimethylbenzonitrile (prepared by N-bromosuccinimide bromination of 2,4,6-trimetbylbenzonitrile). The mixture was treated with boron tribromide according to methods analogous to those described in Example 7 followed by chromatography on a prep plate (silica gel, hexanes-isopropyl alcohol (97:3, 2×developed)) to afford 2-[4-(5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-4,6-dimethylbenzonitrile, m.p. 136° C.-138° C., and 4-[4-(5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-2,6-dimethylbenzonitrile, m.p. 152° C.-154° C. Methylation of 2-[4-(5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-2trifluoromethylpentyl]-4,6-dimethylbenzonitrile and 4-[4-(5 fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-2,6-dimethylbenzonitrile by analogous methods described in Example 8 gave the title compounds 2-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-4,6-dimethylbenzonitrile, m.p. 134° C.-136° C., and 4-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-2,6-dimethylbenzonitrile, m.p. 113° C.-115° C.

Provenance & Evidence