Hydrochloric Acid → 2-Amino-5-bromo[1,1'-biphenyl]-3-sulphonic acid

Participants

Reaction Conditions

Reaction Steps

To a mixture of 37.8 g (100 mmol) of 2-amino-5-bromo-3-iodobenzenesulphonic acid and 32 g (300 mmol) of sodium carbonate in 300 ml of 1,2-dimethoxyethane and 150 ml of water are successively added, under a nitrogen atmosphere, 5.8 g (5 mmol) of tetrakis(triphenylphosphine)palladium (0) and 19.5 g (160 mmol) of benzeneboronic acid. The mixture is heated at the reflux temperature for 4 hours and the reaction medium is then concentrated under reduced pressure. The residue thus obtained is then dissolved in a mixture containing 300 ml of methanol, 300 ml of 0.1N hydrochloric acid and 16 ml of 95% sulphuric acid. The mixture is concentrated to 100 ml under reduced pressure, cooled to 0° C. and filtered. The residue is purified by chromatography on an RP 18 reverse-phase column, eluting with an acetonitrile:water mixture (2:8).

Provenance & Evidence