Sodium Carbonate → Methyl 2-(4-fluorophenyl)-4-methylbenzoate

Participants

Reaction Steps

Tetrakis(triphenylphosphine)palladium (9 g; 7.8 mmol) and ethanol (780 ml) was added to a suspension of methyl 4-methyl-2-trifluoromethanesulphonyloxybenzoate (58 g; 0.195 mol), 2M aqueous solution of sodium carbonate (250 ml; 0.5 mol), 4-fluorophenylboronic acid (30 g; 0.214 mol) and lithium chloride (16.5 g; 0.39 mol) in toluene (1.65 ml), under argon atmosphere. The mixture was refluxed for 4 hours, diluted with ethyl acetate (1 l), washed with aqueous sodium hydroxide solution 1N (1 l). The organic phase was evaporated and the residue purified by flash chromatography (ethyl acetate/petroleum ether: 95/5) to give methyl 2-(4-fluorophenyl)-4-methylbenzoate (46.8 g; 99%).

Provenance & Evidence