1-(9,10-Dihydrophenanthren-2-yl)ethanone → 2-Bromoethyl-9,10-dihydrophenanthrene

Participants

Reaction Steps

To a stirred solution of 5.56 (25 mmol) of (8) in 100 mL of THF, 9.78 g (26 mmol) of phenyltrimethylammonium tribromide was added. After stirring for 20 min, the solution became pale yellow and a precipitate of phenyltrimethylammonium bromide separated. Water (300 mL) was added and the mixture was extracted with ethyl acetate. The extract was washed with water and evaporated to dryness to yield (28) which was further purified by trituration with ether and recrystallized from methanol to furnish pure (28), 5.66 g; m.p. 82°-83° C.

Provenance & Evidence