1-Bromo-4-methylnaphthalene → HCID 20363803, compound

Participants

Reaction Steps

To a stirred solution of butyl lithium (12.5 ml, 0.03 mole, 2.4M solution in hexane) was added dropwise over 20 minutes a solution of 1-bromo-4-methylnaphthalene (6.63 g, 0.03 mole) in dry tetrahydrofuran (10 ml), the reaction mixture being cooled throughout by a water bath. After being stirred at ambient temperature for 15 minutes the resulting suspension was treated with a solution of 2,2-dimethyl-7-(2-dimethylaminoethoxy)-4-chromanone (4.0 g, ~0.015 mole) in dry tetrahydrofuran (15 ml), the precipitate almost immediately dissolving to give a golden yellow solution. The resulting solution was stirred under reflux for 5 hours, then left overnight at ambient temperature, stirred under reflux for a further 7 hours and again left overnight at ambient temperature. After work up with acid, by an analogous process to that described in Example 1 and chromatography on alumina in 8% ether - 92% petroleum ether (b.p. 60°-80°) the title compound was obtained as a colourless oil (0.65 g, 11%). Its hydrochloride salt was m.p. 215°-216.5° C.

Provenance & Evidence