反应详情

温度

-5 °C

A suspension of 10.0 g (54.6 mmol) of 4-methyl-2'-amino-1,1'-biphenyl in 135 mL of water containing 15 mL of concentrated hydrochloric acid was cooled at -5° C. and treated dropwise with a solution of 3.94 g (57.1 mmol) of sodium nitrite in 9.24 mL of water while maintaining the temperature below 0° C. After the addition was complete, the reaction mixture was stirred an additional 10 minutes. The reaction mixture was slowly poured into a vigorously stirred solution of 29.6 g (178 mmol) of potassium iodide and 643 mg (2.5 mmol) of iodine dissolved in 80 mL of water. When the addition was complete, the reaction mixture was slowly warmed to 35° C. and stirred for an additional 25 minutes. The reaction mixture was cooled, and extracted with ethyl ether. The combined extracts were washed with aqueous 10% sodium thiosulfate (3×). aqueous saturated sodium bicarbonate (1×), and water (1×). The extracts were dried over magnesium sulfate, filtered and evaporated under vacuum to yield 14 g of crude product. The product was purified by chromatography over silica gel, eluting with hexanes to yield 9.34 g (31.8 mmol, 58%) of the product. FAB-MS: calculated for C13H11I 294; found 295 (M+1). 1H NMR (200 MHz, CDCl3): 2.42 (s, 3H): 7.14 (dt, 1H), 7.32 (m, 5H), 7.95 (dd, 1H).

1. temperaturewhile maintaining the temperature below 0° C
2. additionAfter the addition
3. additionWhen the addition
4. temperaturethe reaction mixture was slowly warmed to 35° C.
5. stirringstirred for an additional 25 minutes
6. temperatureThe reaction mixture was cooled
7. extractionextracted with ethyl ether
8. washThe combined extracts were washed with aqueous 10% sodium thiosulfate (3×)
9. dry with materialThe extracts were dried over magnesium sulfate
10. filtrationfiltered
11. customevaporated under vacuum
12. customto yield 14 g of crude product
13. customThe product was purified by chromatography over silica gel
14. washeluting with hexanes