反应详情

A mixture of 20 g of 4-bromo-3-methyl-phenylamine, 6.6 g of ferrous sulfate, 40.8 g of propane-1,2,3-triol, 8.12 g of nitrobenzene and 23 ml of concentrated sulfuric acid were heated gently. After the first vigorous reaction, the mixture was heated to reflux for 3 h and then evaporated to remove the excess nitrobenzene. To the solution was added saturated NaHCO3 to pH 8 and the solution was filtered and extracted with dichloromethane. The dichloromethane layers were combined and dried over Na2SO4 and concentrated. The solid was purified via flash column chromatography to give yellow solid which was washed with petroleum ether to return the title compound (7.5 g, 65%). NMR (CDCl3, 300 MHz) δ 8.89 (m, 1H), 8.04 (m, 2H), 7.96 (s, 1H), 7.36 (m, 1H), 2.60 (s, 3H).

1. temperaturewere heated gently
2. customAfter the first vigorous reaction
3. temperaturethe mixture was heated
4. temperatureto reflux for 3 h
5. customevaporated
6. customto remove the excess nitrobenzene
7. additionTo the solution was added saturated NaHCO3 to pH 8
8. filtrationthe solution was filtered
9. extractionextracted with dichloromethane
10. dry with materialdried over Na2SO4
11. concentrationconcentrated
12. customThe solid was purified via flash column chromatography
13. customto give yellow solid which
14. washwas washed with petroleum ether