Dichloromethane → Methyl 6-methyl-4'-trifluoromethylbiphenyl-2-carboxylate

Participants

Reaction Steps

A mixture of methyl 2-bromo-3-methylbenzoate (22.33 g, 97.5 mmol), potassium phosphate (82.8 g, 390 mmol), [1,1′-bis(diphenylphosphino)-ferrocene]dichloro palladium (II), complex with dichloromethane (1:1) (3.98 g, 4.87 mmol), and p-trifluoromethylphenylboronic acid (22.2 g, 117 mmol) in 500 mL of DME is degassed and refluxed under an atmosphere of argon overnight. The mixture is concentrated, poured into water and extracted with ethyl acetate. The combined organic extracts are washed with brine, dried over magnesium sulphate, filtered and evaporated under reduced pressure. The residue is purified by silica gel chromatography eluting with ethyl acetate/toluene (1:9) to give methyl 6-methyl4′-trifluoromethyl-biphenyl-2-carboxylate.

Provenance & Evidence