4,4'-Dibromobiphenyl → HCID 20650340, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of tris(dibenzylideneacetone)dipalladium (353 mg, 0.385 mmol), and tri-tert-butyl phosphine (3.11 g of a 10% solution in hexanes) was degassed in toluene (anhydrous, 50 mL) for 20 minutes. Di-p-tolylamine (3.00 g, 15.2 mmol), and 4, 4′-dibromobiphenyl (4.80 g, 15.4 mmol) were added and the mixture was further degassed for 15 minutes. Sodium tert-butoxide (2.4 g, 25 mmol) was added, and mixture was further degassed for 10 minutes. The whole was heated overnight at 120° C. under argon. After cooling, the mixture was poured into dichloromethane (DCM), and solids were filtered off. Filtrate was washed with water and brine. The organic layer was collected and dried over sodium sulfate, then loaded onto silica gel. A flash column (gradient of 2-20% ethyl acetate in hexanes) gave 190 mg of material (3% yield); confirmed pure by HNMR.

Provenance & Evidence