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

HRID 720562Notes

Reaction equation

HRID 720562 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. 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.

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. 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.

Sources & evidence

ORD record
ord-df695f71b5944581aec0a22f9635373e
Source dataset
uspto-grants-2006_11
Patent number
US07135487B2

Reaction notes

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