反应详情

To a solution of 1-iodo-3-methoxy-5-nitro-benzene (8.2 g, 29.39 mmol) in methylene chloride (600 mL) was added 1.0 M solution of borontribromide (58.78 mL, 58.78 mmol) in methylene chloride at −78° C. The resulting solution was stirred for 30 minutes and then the cooling bath was removed to warm to room temperature. After stirring for 15 h at this temperature, the reaction mixture was heated to reflux for 4 h in order to complete the reaction. Then, it was cooled to room temperature and diluted with water (100 mL) and the methylene chloride was removed under vacuum. Then, the organic compound was extracted into diethyl ether (2×100 mL) and the combined ether extracts were washed with brine solution (200 mL). Then, the organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by using an ISCO 120 g column, eluting with 0-15% ethyl acetate in hexanes to obtain 3-iodo-5-nitro-phenol (4.8 g, 62%) as a light yellow solid: ES(+)-HRMS m/e calculated for C6H4INO3 (M−H)+ 263.9163, found 263.9162.

1. customthe cooling bath was removed
2. stirringAfter stirring for 15 h at this temperature
3. temperaturethe reaction mixture was heated
4. temperatureto reflux for 4 h in order
5. customthe reaction
6. temperatureThen, it was cooled to room temperature
7. customthe methylene chloride was removed under vacuum
8. extractionThen, the organic compound was extracted into diethyl ether (2×100 mL)
9. washthe combined ether extracts were washed with brine solution (200 mL)
10. dry with materialThen, the organic layer was dried over anhydrous magnesium sulfate
11. filtrationfiltered
12. concentrationconcentrated in vacuo
13. customThe crude residue was purified
14. washeluting with 0-15% ethyl acetate in hexanes