2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1,1':4',1''-Terphenyl, 2'-fluoro-4''-propyl-

Participants

Reaction Conditions

Reaction Steps

A solution of 4-(4-n-propylcyclohexenyl)-2-fluorobiphenyl (20 gram) in toluene (120 ml) was added over a 25 minute period with stirring to a suspension of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (34 gram) in toluene (200 ml). The temperature rose from 19° C. to 24° C. over the addition, after which time the reaction mixture was heated under reflux (114° C.) for 3 hours. The reaction mixture was cooled, filtered, the filtrate and toluene washings (100 ml) were combined and then washed with saturated sodium metabisulphite solution (250 ml). The organic extract was further washed with water (2×250 ml), dried and evaporated to dryness to give a brown residue (20.1 gram). The residue was dissolved in dichloromethane (120 mls) and adsorbed onto a column of basic alumina (60 gram) over silica gel (60 gram). Elution with dichloromethane (450 ml) gave on evaporation of the solvent an off white solid (14 gram) which was recrystallised from ethanol (80 mls) to yield a white crystalline product (12.8 gram) m.p. 75°-77° C.

Provenance & Evidence