3-Carboxyphenylboronic acid → 2'-Methoxy-3'-nitrobiphenyl-3-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

1-Bromo-2-methoxy-3-nitro-benzene 1c (23.25 g, 0.10 mol), 3-carboxyphenylboronic acid (19.5 g, 0.117 mol) and tetrakis(triphenylphosphine)palladium (8.86 g, 7.7 mol) were dissolved in a solvent mixture of 100 mL of 2 N aqueous sodium carbonate and 500 mL of 1,4-dioxane. The reaction mixture was heated to reflux at 105° C. for 43 hours. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was concentrated under reduced pressure and then 300 mL of 6 N hydrochloric acid and 400 mL of ethyl acetate were added. The aqueous layer was extracted with ethyl acetate (200 mL×2). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to obtain the title compound 2′-methoxy-3′-nitro-biphenyl-3-carboxylic acid 1d (53.93 g) as a light yellow solid.

Provenance & Evidence