반응 #468154

반응 방정식

4-Bromoaniline

2,5-hexanedione

acetic acid

→

1-(4-bromophenyl)-2,5-dimethylpyrrole

용매

Toluene

반응 조건

후처리

1. 1
   온도heated
2. 2
   온도under reflux for 8 hours
3. 3
   기타to remove the water
4. 4
   기타from the reaction
5. 5
   농축concentrated under reduced vacuum
6. 6
   세척washed one time each with 2N hydrochloric acid, 2N NaOH, and H2O
7. 7
   건조dried over Na2SO4
8. 8
   농축concentrated under reduced vacuum
9. 9
   기타to yield a brown solid
10. 10
    기타Material was purified by silica gel flash chromatography
11. 11
    세척eluting with hexane
12. 12
    기타Concentration of the appropriate fractions yielded 55.0 gm

실험 절차

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.

출처