2-Iodobenzoic acid → 2-(3-methylphenyl)benzoic Acid

Participants

Reaction Steps

In an oven dried flask flushed with N2 was combined 2.7 g (20.0 mmol) of 3-methylbenzeneboronic acid, 3.64 g (15 mmol) of 2-iodobenzoic acid, 150 mL of DME, 26 mL of 10% Na2CO3 and 600 mg (0.5 mmol) of Pd(PPh3)4. The mixture was warmed to reflux for 24 h and partitioned between 100 mL of NaHCO3 and 100 mL of ether. The ether layer was extracted with 2×50 mL of NaHCO3 and the combined NaHCO3 fractions were washed with 2×50 mL of ether, acidified with 10% HCl and extracted with 3×75 mL of ether. The combined ether extracts were washed with 50 mL of H2O, 50 mL of brine, dried (MgSO4) and concentrated in vacuo. The oil was crystallized from ether/hexanes (1/1) at -20° C. as a white precipitate, which after filtration, provided 1.32 g (41% yield) of 3'-methyl-2-biphenylcarboxylic acid as a brown oil.

Provenance & Evidence