3-Nitrophenylboronic Acid → HCID 57143370, compound

Participants

Reaction Steps

To a solution of methyl,5-chloro-3-iodo-2-methoxybenzoic acid methyl ester (0.80 g, 2.5 mmol) and tetrakis (triphenylphosphine)palladium(0) (0.085 g, 0.074 mmol) in toluene (12 mL) was added 3-nitrobenzene-boronic acid (0.45 g, 2.7 mmol) dissolved in 1 mL of ethanol. Aqueous 2 N K2CO3 (2.7 mL, 5.4 mmol) was added and the mixture was heated to reflux for 18 h. The mixture was diluted with ether, washed with 3:1 saturated NaHCO3/conc. ammonium hydroxide, 0.1 M EDTA, saturated NaCl, and dried (Na2SO4). The solvent was removed under reduced pressure, and the crude material was purified by silica gel chromatography employing a gradient elution of 60 to 75% CH2Cl2/hexane. 5-Chloro-2-methoxy-3′-nitro-biphenyl-3-carboxylic acid methyl ester 43 was obtained as an amber waxy solid (0.59 g, 75% yield).

Provenance & Evidence