Sodium Carbonate → [1,1'-Biphenyl]-3-carboxylic acid, 2'-methoxy-, methyl ester

Participants

Reaction Steps

Methyl 3-bromobenzoate (1.99 g, 9.25 mmol), tetrakis(triphenylphosphine) palladium(O) (110 mg), sodium carbonate (2.04 g, 19 mmol in 5 ml water) and toluene (10 ml) were degassed under nitrogen in a 25 ml flask fitted with a reflux condenser. 2-Methoxybenzeneboronic acid (1.46 g, 9.61 mmol) in toluene (1 ml) was added and the mixture was heated at reflux for two days then mixed with 1:1 saturated sodium chloride/ethyl acetate (15 ml). The organic materials were separated, dried (MgSO4) then concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, gradient hexane to 8:1 hexane/ethyl acetate) which gave methyl 3-(2-methoxyphenyl)benzoate (1.43 g, 64%), m.p.: 92°-93° C.

Provenance & Evidence