Diisopentyl ether → 2,3-Diphenyl-1,1-bis(3,5-dibromophenyl)-1H-indene

Participants

Reaction Steps

A mixture of bromotriphenylethylene (14.143 g, 42.19 mmol), magnesium (903 mg, 37.2 mmol) and i-pentylether (100 cm3) was heated to reflux for 1.75 h. Heating was temporarily removed and 1 (14.00 g, 28.12 mmol) was added. The mixture was heated to reflux under nitrogen for 20 h and then allowed to cool. Hexane (100 cm3) was added and the mixture was allowed to stand for 30 min. The resultant precipitate was collected and washed with hexane. The solid was mixed with dichloromethane (200 cm3) and aqueous ammonium chloride (1 M, 200 cm3) and stirred until fully dissolved. The aqueous layer was separated and extracted with dichloromethane (3×30 cm3) and the combined organic layers washed with aqueous ammonium chloride (1 M, 100 cm3) and water (100 cm3), dried over anhydrous magnesium sulphate, filtered and the solvent removed. The residue was triturated with boiling ethanol, cooled and filtered to give 2 (16.34 g, 79%) as a white solid.

Provenance & Evidence