Chloride → 4-Fluoro-2-iodotoluene

関与物質

反応条件

反応手順

2-Amino-4-fluorotoluene (68 g) is added dropwise to a stirred solution of 100 ml hydrochloric acid in 700 ml of water and after cooling to 0°-5° C., a solution of 46 g sodium nitrite in 100 ml water was slowly added dropwise. The resultant ice-cold solution of the diasonium chloride was added over 1 hour with stirring to a solution of 157 g potassium iodide and 35 ml of sulfuric acid in 250 ml water at 20°-25° C. The mixture was then stirred and heated for 2 hours at 100° C. After cooling, an oily product was separated and the remaining aqueous layer extracted with benzene. The separated product was dissolved in the benzene layer, the solution washed with a 5% sodium hydrogen sulfite solution, with water, 5% sodium hydroxide solution and again with water, dried with magnesium sulfate and filtered with charcoal. From the filtrate, benzene was evaporated under reduced pressure and the residue distilled. There were obtained 105.3 g of 2-iodo-4-fluorotoluene boiling at 92°-95° C./17 Torr.

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