Hydrochloric Acid → 1-o-Biphenylyl-3-phenylisobenzofuran

Participants

Reaction Conditions

Reaction Steps

In Ar, 3.9 g (1.68E-2 mol) of o-bromobiphenyl was dissolved in 30 cm3 of tetrahydrofuran (THF) at −50° C. To the solution was added 10 cm3 of a nBuLi hexane solution (1.5 mol/l). After 2 hours, 3 g (1.4E-2 mol) of 3-phenylphthalide was added to the solution while it was kept cooled at −50° C. After 2 hours, the reaction solution was allowed to resume room temperature, and 10 cm3 of a 35% aqueous hydrochloric acid was added thereto. After 1 hour, toluene extraction was carried out using a separatory funnel, followed by thorough washing with distilled water. After the toluene solution was concentrated, the end product was isolated by silica gel chromatography (developer, toluene:hexane=1:4). There was obtained 4 g (80%) of a yellow viscous substance emitting bluish green fluorescence.

Provenance & Evidence