Water → 1-(2,6-Dichloro-4-trifluoromethylphenyl)-2,5-dimethylpyrrole

HRID 2082105Notes

Reaction equation

HRID 2082105 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[C:5]([Cl:13])[C:3]=1[NH2:4].O.[C:15]1(C)[CH:20]=[CH:19][C:18](S(O)(=O)=O)=[CH:17][CH:16]=1.C(CC(=O)C)C(C)=O.O>C1C=CC=CC=1>[Cl:1][C:2]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[C:5]([Cl:13])[C:3]=1[N:4]1[C:17]([CH3:18])=[CH:16][CH:15]=[C:20]1[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 80352,5-HexanedioneHCID 1410944-Amino-3,5-dichlorobenzotrifluorideHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 224183221-(2,6-Dichloro-4-trifluoromethylphenyl)-2,5-dimethylpyrroleYield 811.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a refluxing solution of 9.20 g (40.0 mmoles) of 2,6-dichloro-4-trifluoromethylaniline and 0.76 g (4.0 mmoles) of p-toluenesulfonic acid monohydrate in 25 mL of benzene was added dropwise over an 8 hour period with a syringe pump 9.40 mL (9.14 g, 80.1 mmoles) of acetonylacetone. Throughout the addition, water was removed via a Dean-Stark trap. The reaction mixture was then cooled and partitioned with a saturated aqueous solution of NaHCO3 which was back-extracted with ether. The combined organic layers were dried over anhydrous Na2SO4 concentrated. The residual brown oil was chromatographed on silica gel with a 95:5 v/v hexane-EtOAc eluent to afford 10.0 g (81%) of 1-(2,6-dichloro-4-trifluoromethylphenyl)-2,5-dimethylpyrrole as a light brown solid of melting point 63° C.

Workup

  1. customwas removed via a Dean-Stark trap
  2. temperatureThe reaction mixture was then cooled
  3. custompartitioned with a saturated aqueous solution of NaHCO3 which
  4. extractionwas back-extracted with ether
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customThe residual brown oil was chromatographed on silica gel with a 95:5 v/v hexane-EtOAc eluent

Sources & evidence

ORD record
ord-f33fb351dbe84ecd8a4de902a259f885
Source dataset
uspto-grants-1993_02
Patent number
US05187185

Reaction notes

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