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 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 combined organic phases were washed with 1 M aqueous sodium hydroxide (500 mL) and brine (500 mL), dried over anhydrous potassium carbonate, filtered and concentrated in vacuo to afford a dark oil (28.6 g). Purification by flash chromatography using 2% ethyl acetate in hexanes as solvent provided the title compound (24.7 g) as a pale yellow oil.

Provenance & Evidence