Hydrochloric Acid → 1-Iodo-4-(trifluoromethoxy)benzene

Participants

Reaction Conditions

Reaction Steps

4-Trifluoromethoxyaniline (29.0 g.) was added at 0° C. to concentrated hydrochloric acid (160 mls.) and the thick white suspension so obtained was cooled to -5° C. The suspension was diazotised by adding a solution of sodium nitrite (13.0 g.) in water (20 ml.) over 20 minutes, keeping the temperature below 0° C. After 2 hours at 0° C., the suspension was added portionwise to a solution of potassium iodide (40 g.) and iodine (60 g.) in water (260 ml.) at 10° C. and the solution was allowed to stand at room temperature for 1 hour. The dark solution so obtained was extracted with diethyl ether three times, and the combined ether extracts were washed sequentially with sodium sulphite, water and brine, and on evaporation gave a golden oil which was distilled under water pump pressure to give 4-trifluoromethoxyiodobenzene as a pale pink liquid, b.p. 107°-8° C.

Provenance & Evidence