反应详情

4-Bromoaniline (56.0 g., 0.33 Mol.), 2,5-hexanedione (37.6 g., 0.33 Mol), and acetic acid (5 ml) were placed into Toluene (500 ml) and heated under reflux for 8 hours employing a dean stark trap to remove the water from the reaction. The reaction was cooled to room temperature and concentrated under reduced vacuum. The resulting oil was taken into ethyl acetate, washed one time each with 2N hydrochloric acid, 2N NaOH, and H2O, dried over Na2SO4, and concentrated under reduced vacuum to yield a brown solid. Material was purified by silica gel flash chromatography eluting with hexane. Concentration of the appropriate fractions yielded 55.0 gm. of a light yellow solid. (68%) NMR was consistent with the proposed title structure. Field Desorption Mass Spectrum:M+249 m.p. 71°–73° C.

1. temperatureheated
2. temperatureunder reflux for 8 hours
3. customto remove the water
4. customfrom the reaction
5. concentrationconcentrated under reduced vacuum
6. washwashed one time each with 2N hydrochloric acid, 2N NaOH, and H2O
7. dry with materialdried over Na2SO4
8. concentrationconcentrated under reduced vacuum
9. customto yield a brown solid
10. customMaterial was purified by silica gel flash chromatography
11. washeluting with hexane
12. customConcentration of the appropriate fractions yielded 55.0 gm
13. custom71°–73° C.