1,2-Dimethoxyethane → Biphenyl

Participants

Reaction Conditions

Reaction Steps

A degassed solution of 2-bromo tert-butylbenzenesulfonamide (IV) (15.6 g, 53.5 mmol) and tetrakis(triphenylphosphine)palladium (3.1 g, 2.7 mmol) in dimethoxyethane (270 mL) was stirred at room temperature for 5 minutes. Boronic acid V (purchased from Omega Chemical Company Inc.) (10 g, 53.5 mmol) and a 2M solution of sodium bicarbonate (53 mL) were then added and the mixture was heated to 90° C. and stirred at this temperature for 24 hours. The mixture was then cooled down and a saturated solution of ammonium chloride (300 mL) and ethyl acetate (300 mL) were added. The separated aqueous layer was extracted with ethyl acetate (3×100 mL) and the combined organic layers were dried (MgSO4 anh.), filtered and evaporated. Flash chromatography of the residue (EtOAc-hexanes 1:1) yielded biphenyl compound VI.

Provenance & Evidence