反应详情

4-Azido-3-chlorotoluene (17.14 g, 0.1 mol) was dissolved in dry benzene (80 ml) and thereto were added N-bromosuccinimide (19.6 g, 0.11 mol) and AIBN (1.64 g, 0.01 mol). The resulting mixture was refluxed in the shade in a nitrogen stream for 10 hr. Water (100 ml) was added and the mixture was filtrated. The aqueous layer of the filtrate was taken and extracted with ether. The organic layers were combined, washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained brown oil was purified by silica gel column chromatography (eluent; hexane) to give the title compound (14.2 g, yield 58%). m.p.: 75-77° C.

1. temperatureThe resulting mixture was refluxed in the shade in a nitrogen stream for 10 hr
2. filtrationthe mixture was filtrated
3. extractionextracted with ether
4. washwashed with brine
5. dry with materialdried over anhydrous sodium sulfate
6. customThe solvent was evaporated under reduced pressure
7. customthe obtained brown oil was purified by silica gel column chromatography (eluent; hexane)