Potassium Carbonate → Methyl 2,2'-dimethyl-1,1'-biphenyl-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 4-bromo-3-methylbenzoate (25.0 g, 110 mmol), o-tolylboronic acid (16.5 g, 120 mmol) and potassium carbonate (50 g, 360 mmol) in dioxane:water (300 mL: 200 mL) was purged with nitrogen for 1 hour. [1,1′bis(Diphenylphosphino)ferrocene]dichloropalladium[II] (4.5 g, 5.5 mmol) was added and the reaction mixture was heated to 100° C. with vigorous stirring for 3.5 hours. The cooled reaction mixture was filtered through Celite and the cake washed with ethyl acetate (500 mL). The organic phase was separated, washed with 1 M sodium hydroxide (500 mL) and brine (500 mL), dried over anhydrous potassium carbonate and concentrated in vacuo to give the crude product as a dark oil (28.6 g). Purification by flash chromatography using a solvent gradient of 2% ethyl acetate in hexane afforded the title compound (24.7 g, 93%) as a pale yellow oil.

Provenance & Evidence