1-Bromonaphthalene → HCID 20363807, compound

Participants

Reaction Steps

1-Naphthylmagnesium bromide was prepared by the addition of 1-bromonaphthalene (9.6 g, 0.046 mole) to magnesium (1 g) in tetrahydrofuran (25 ml). 6-(2-dimethylaminoethoxy)-1-tetralone (9.8 g, 0.046 mole) in tetrahydrofuran 75 ml) was added over 1/2 hour and the reaction mixture refluxed for 2 hours. After cooling, saturated ammonium chloride solution was added and the organic layer separated. Removal of the solvent gave an oil which after chromatography on alumina, eluting with ether - light petroleum (b.p. 60°-80°) gave 1-(1-naphthyl-3,4-dihydro-6(2-dimethylaminoethoxy)naphthalene (2.0 g, 15%) as a colourless oil which was converted to the hydrochloride salt m.p. 168°-170° C.

Provenance & Evidence