Dimethylformamide → 2-bromo-6-butoxynaphthalene

Participants

Reaction Steps

An oil dispersion of 480 mg (50%, 10 mmol, Alfa) of sodium hydride was washed three times with petroleum ether then the residue covered with 5 ml of dry THF. To the resulting stirred slurry was added dropwise a solution of 2.00 g (8.97 mmol, Aldrich) of 6-bromo-2-naphthol, in 10 ml of THF over 10 minutes. The reaction mixture was stirred for 30 minutes then 1.70 g (9.23 mmol, Aldrich) of 1-iodobutane and 15 ml of sieve-dried DMF were added. The resulting solution was heated to 60° for two hours, then cooled, added to 100 ml of H2O and extracted with 50 ml of petroleum ether. The organic extract was washed with an additional 100 ml of H2O, dried (MgSO4) and concentrated in vacuo to give a solid. The crude material was purified by flash chromatography (15×5 cm, pet ether) to afford 2.31 g (92%) of title compound as a white solid, m.p. 48°-50°.

Provenance & Evidence