Hydrochloric Acid → HCID 58123258, compound

Participants

Reaction Conditions

Reaction Steps

4.95 ml (15% solution in n-hexane) of n-butyllithium are added to a solution, cooled to −78° C., of 1.03 ml (7.23 mmol) of 4-bromophenetole in 35 ml of tetrahydrofuran under nitrogen, and the mixture is stirred at −78° C. for one hour. A solution of 1.4 g (6.6 mmol) of 5-bromobenzofuran-3-one is subsequently added dropwise at such a rate that the temperature does not rise above −70° C., stirring is continued at −78° C. for one hour, the reaction mixture is then allowed to come to room temperature stirred at room temperature for a further 15 hours, finally 10 ml of 1N hydrochloric acid are added, and stirring is continued for a further one hour. After addition of 20 ml of water, the tetrahydrofuran is stripped off in vacuo, and the aqueous mixture remaining is extracted three times with 10 ml of diethyl ether each time. After the combined organic phases have been washed with 10 ml of saturated sodium chloride solution and after drying over sodium sulfate, the solvent is stripped off in a rotary evaporator, and the crude product is purified by column chromatography on silica gel (petroleum ether/ethyl acetate 98:2), giving 0.95 g of 5-bromo-3-(4-ethoxyphenyl)-benzofuran as colourless oil; LC/MS: 318 (M+H);

Provenance & Evidence