Acetic Acid → 1-(4-Bromophenyl)-2,5-Dimethyl-1H-Pyrrole

HRID 1167216Notes

Reaction equation

HRID 1167216 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH3:9][C:10](=O)[CH2:11][CH2:12][C:13](=O)[CH3:14].C(O)(=O)C>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]2[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 78074-BromoanilineHCID 80352,5-Hexanedione

Product 1

HCID 27396091-(4-Bromophenyl)-2,5-Dimethyl-1H-Pyrrole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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. The material was purified by silica gel flash chromatography eluting with hexanes. Concentration of the appropriate fractions yielded 55.0 gm. of a light yellow solid. (68%) The NMR spectrum was consistent with the proposed title structure. Field Desorption Mass Spectrum: M+ 249 m.p. 71°-73° C.

Workup

  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. customThe material was purified by silica gel flash chromatography
  11. washeluting with hexanes
  12. customConcentration of the appropriate fractions yielded 55.0 gm
  13. custom71°-73° C.

Sources & evidence

ORD record
ord-cd16c76e0aac46e2863c953d6fb238f8
Source dataset
uspto-grants-2003_09
Patent number
US06617351B1

Reaction notes

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