Water → 1-Bromo-4-(pentyloxy)benzene

Participants

Reaction Steps

To a solution of 1.44 g (6.92 mmol) of a subtitled compound of Preparation 2B in 50 ml of toluene and 20 ml of methanol under nitrogen, was added 15.5 ml (31.1 mmol) a 2M sol. of sodium carbonate which resulted in the formation of a white precipitate. To the resultant mixture, was added 800 mg (0.69 mmol) of palladium tetrakis (triphenylphosphine), followed by 1.64 g (6.92 mmol) of 2,5-dibromopyridine. The resultant reaction mixture was reacted for approximately three hours, forty-five minutes at reflux temperature. When the reaction was substantially complete, as indicated by TLC, the mixture was cooled to room temperature and allowed to stir overnight. The reaction mixture was placed in a separatory funnel and combined with diethyl ether and water. The resultant layers were separated and the organic layer was dried over sodium sulfate, filtered and then concentrated in vacuo to provide a residue. This residue was redissolved in pentane and filtered to provide 0.95 g of the desired compound. The filtrate was recrystallized to provide an additional 1.4 g of the desired compound. These solids were combined and used without further purification. ##STR20##

Provenance & Evidence