反应详情

Sodium iodate (158 g, 0.800 mol, 0.4 eq.) was added portionwise, under nitrogen atmosphere, to an ice-cooled mixture of 4-chloro-2-nitrotoluene (343 g, 2.00 mol), iodine (204 g, 0.800 mol, 0.4 eq.) and conc. sulfuric acid (1960 g, 20.0 mol, 10 eq.) and the resulting mixture was stirred at a temperature of 5° C. to 10° C. for 6 hours. Water (2 L) was added dropwise thereto with stirring in an ice-water bath, and the mixture was extracted with toluene (2.5 L). The combined organic layer was treated with aqueous 10% sodium thiosulfate solution, washed with water (1 L×2) and aqueous sat. sodium hydrogencarbonate solution (1 L×2) successively, dried over sodium sulfate and concentrated to give crude A-1 (548 g, purity 62%) as a yellow oil. This product was used in the following reaction without further purification.

1. temperaturecooled
2. stirringwith stirring in an ice-water bath
3. extractionthe mixture was extracted with toluene (2.5 L)
4. additionThe combined organic layer was treated with aqueous 10% sodium thiosulfate solution
5. washwashed with water (1 L×2) and aqueous sat. sodium hydrogencarbonate solution (1 L×2) successively
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated
8. customto give crude A-1 (548 g, purity 62%) as a yellow oil
9. customThis product was used in the following reaction without further purification