Hydrogen Bromide → HCID 66704062, compound

Participants

Reaction Steps

To a solution of sodium nitrite (1.40 g) in dimethyl sulfoxide (50 mL) is added 2′-amino-4′-methoxy-biphenyl-4-carboxylic acid methyl ester (2.61 g). After 5 minutes, the reaction mixture is treated with a solution of 4.7 mL hydrobromic acid (48%) in 50 mL dimethyl sulfoxide. The reaction is allowed to stir at room temperature for 2 h. The reaction mixture is diluted with a solution of 20.0 g potassium carbonate dissolved in 400 mL water. The product is extracted five times with methylene chloride. The combined organic layers are dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue is purified via flash chromatography eluting with hexanes/ethyl acetate (99:1 to 86:14) to afford the title compound (1.00 g, 31%) as a white solid.

Provenance & Evidence