alpha-Bromo-o-chlorotoluene → 9-[(2-Chlorophenyl)methyl]-6,8-difluoro-2,3,4,9-tetrahydro-1H-carbazole-1-acetic acid

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Reaction Steps

A solution of 200 mg of 6,8-difluoro-1,2,3,4-tetrahydrocarbazol-1-yl-acetic acid from Example 30 Step II in 8 cc of DMF was added portionwise 40 mg of sodium hydride. The resulting mixture was stirred for 30 min. at room temperature and 185 mg of o-chlorobenzyl bromide was then added. After stirring overnight at room temperature, the resulting mixture was diluted with water and washed with ether. The aqueous layer was acidified with (1N) HCl and extracted with ether. The ethereal layer was washed with brine, dried over Na2SO4 and evaporated to dryness. The crude product was purified on preparative plates (silica gel) eluting with CHCl3 :MeOH:NH4OH (8:4:1) to yield 98 mg of 9-o-chlorobenzyl-6,8-difluoro-1,2,3,4-tetrahydrocarbazol-1-yl-acetic acid, m.p. 197°-198° C.

Provenance & Evidence