Sodium Carbonate → 2'-Methoxy-5'-methyl-3-nitro-biphenyl-3-carboxylic acid

Beteiligte Stoffe

Reaktionsschritte

1-Bromo-2-methoxy-5-methyl-3-nitro-benzene 11c (15.0 g, 61 mmol) and 3-carboxyphenylboronic acid (11.6 g, 70.1 mmol) were dissolved in 200 mL of 1,4-dioxane followed by addition of tetrakis(triphenylphosphine)palladium (2.8 g, 2.44 mmol) and 61 mL of aqueous sodium carbonate (12.9 g, 122 mmol). The reaction mixture was heated to reflux overnight. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was concentrated under reduced pressure and the residue was diluted with 500 mL of water. The mixture was washed with the solvent mixture of 150 mL of n-hexane and 150 mL of ethyl acetate followed by ethyl acetate (300 mL×2). The aqueous layer was adjusted to pH 1˜2 with concentrated hydrochloric acid. The mixture was filtered and the filter cake was dried to obtain the title compound 2′-methoxy-5′-methyl-3-nitro-biphenyl-3-carboxylic acid 11d (15.4 g, 88.1%) as a yellow solid.

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