Potassium Iodide → 2-Chloro-1-iodo-4-(trifluoromethoxy)benzene

Participants

Reaction Steps

Part B. A solution of the aniline from Part A (17.97 g, 84.9 mmol) in concentrated hydrochloric acid (50 mL) was cooled to −5° C., and treated with a saturated aqueous solution of sodium nitrite (6.45 g, 93.5 mmol) After stirring for 30 min., the solution was diluted with 50 mL cyclohexane and 50 mL dichloromethane, and the resulting mixture was stirred vigorously while a saturated aqueous solution of potassium iodide (28.2 g, 170 mmol) was added dropwise. The resulting solution was allowed to stir for 12 h, then was partitioned between water and dichloromethane. The organic phase was washed with 1 N aqueous sodium bisulfite solution and brine. The three aqueous phases were back-extracted in sequence with dichloromethane, and the organic phases were combined, dried over anhydrous magnesium sulfate, filtered and evaporated. The product was purified by distillation to afford the product, 3-chloro-4-iodo-trifluoroanisole (21.38 g, 66.3 mmol, 78%). b.p. 60-70° C./l mm Hg (bulb-to-bulb). 1H NMR (300 MHz, CDCl3): Δ 7.87 (1H, d, J=8.8 Hz), 7.35 (1H, d, J=2.5 Hz), 6.87 (1H, J=ddd, J=8.8 Hz, 2.5H, 0.7 Hz). MS (H2O-GC/MS): m/e 324 (31), 323 (10), 322 (100).

Provenance & Evidence