Potassium Carbonate → 4-Bromotriphenylamine

Participants

Reaction Steps

A mixture of 1-bromo-4-iodobenzene (11.30 g., 40 mmol.), diphenylamine (6.65 g., 39.3 mmol.), powdered potassium carbonate (26.6 g., 192.7 mmol.), 18-crown-6 (1.06 g., 4 mmol.), copper bronze (1.37 g., 21.6 mmol.), and 1.2-dichlorobenzene (40 ml) was kept at 190° C., cooled and filtered. The residue left on concentration of filtrate, was chromatograhped on silica gel. After elution with hexanes (1 liter), the product came out in 9:1 toluene hexanes eluates, and was isolated as a colorless solid after trituration with methanol, 4.47 g. (35% yield), m.p. 113-115° C. Mass Spec (m/z): 371 (M+iodotriphenylamine), 323 325 (M+).

Provenance & Evidence