Nitrobenzene → 3,6-Dibromo-2-phenylazo-phenylamine

Participants

Reaction Conditions

Reaction Steps

3,6-dibromo-1,2-phenylenediamine (1.33 g, 5.0 mmol), nitrobenzene (2.06 mL, 20 mmol), and sodium hydroxide (0.20 g, 5 mmol) were mixed in an 1-neck 100-mL round bottomed flask. The flask was heated in an oil bath at 160° C. for 3 h. The mixture was cooled to room temperature and dichloromethane was added to extract the product. The extract was filtered and the solution concentrated using a rotary evaporator. The solution was chromatographed on a silica gel column using dichloromethane as eluent. The fractions were combined and solvent removed under reduced pressure. The solid was further dried under high vacuum for 1 h. Yield: 3.5%.

Provenance & Evidence