反应详情

A mixture of 3-bromo-2-tert-butylsulfanyl-5-nitro-benzaldehyde oxime (1.98 g, 5.97 mmol) and p-toluenesulfonic acid (567 mg, 2.98 mmol) in n-butanol (20 mL) was heated to reflux for 16 h. The reaction mixture was cooled and concentrated. The residue was treated with water followed by saturated sodium bicarbonate solution and then was extracted with dichloromethane (3×20 mL). The combined organic fractions were washed with water, dried over sodium sulfate, filtered and concentrated. Purification by column chromatography (20% ethyl acetate:hexanes) afforded 1.0 g (65%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 9.21 (s, 1H), 8.95 (s, 1H), 8.59 (s, 1H).

1. temperaturewas heated
2. temperatureto reflux for 16 h
3. temperatureThe reaction mixture was cooled
4. concentrationconcentrated
5. additionThe residue was treated with water
6. extractionwas extracted with dichloromethane (3×20 mL)
7. washThe combined organic fractions were washed with water
8. dry with materialdried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated
11. customPurification by column chromatography (20% ethyl acetate:hexanes)