反应详情

To a suspension of 1-(6-amino-3,3-dimethylindolin-1-yl)ethanone (2.000 g, 9.791 mmol) in concentrated hydrochloric acid (20.00 ml, 548.5 mmol) at 0° was added ice (15 g) followed by a solution of sodium nitrite (0.7769 g, 11.26 mmol) in water (15 mL). After 45 min, a solution of potassium iodide (3.251 g, 19.58 mmol) in water (15 mL) was added dropwise. After 5 min, the mixture was allowed to warm to RT. After 1 hr, CH2Cl2 (ca. 100 mL) and water (ca. 25 mL) were added. The aqueous fraction was extracted 2× with CH2Cl2. The combined organic fractions were washed with saturated NaHCO3 followed by 10% NaS2O3 and brine. After drying with Na2SO4, the deep red solution was concentrated in vacuo and purified by silica gel chromatography using 10-60% hexanes:EtOAc to afford 1-(6-iodo-3,3-dimethylindolin-1-yl)ethanone as an orange oil that solidified upon standing. M+H+=316.0.

1. waitAfter 5 min
2. waitAfter 1 hr
3. extractionThe aqueous fraction was extracted 2× with CH2Cl2
4. washThe combined organic fractions were washed with saturated NaHCO3
5. dry with materialAfter drying with Na2SO4
6. concentrationthe deep red solution was concentrated in vacuo
7. custompurified by silica gel chromatography