Hydrochloric Acid → 1-(5-Acetyl-1H-pyrrol-3-yl)-2,2,2-trichloro-ethanone

HRID 1619078Notes

Reaction equation

HRID 1619078 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:8])[CH3:7].[Cl-].[Cl-].[Cl-].[Al+3].[Cl:13][C:14]([Cl:19])([Cl:18])[C:15](Cl)=[O:16].Cl>ClCCl>[C:6]([C:2]1[NH:1][CH:5]=[C:4]([C:15](=[O:16])[C:14]([Cl:19])([Cl:18])[Cl:13])[CH:3]=1)(=[O:8])[CH3:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6420Trichloroacetyl chlorideHCID 140792-AcetylpyrroleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 666782331-(5-Acetyl-1H-pyrrol-3-yl)-2,2,2-trichloro-ethanoneYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(1H-Pyrrol-2-yl)-ethanone (0.980 g, 8.98 mmol) in dichloromethane (10 mL), anhydrous aluminum trichloride (3.05 g, 22.9 mmol) were added and the suspension was vigorously stirred for 15 minutes. Trichloro-acetyl chloride (1.53 mL, 13.74 mmol) in 7 mL of dichloromethane was slowly added and the mixture was then refluxed for 3 hours. The reaction mixture was cooled and poured into an iced solution of 75 mL of HCl 2N and vigorously stirred for 2 hours. Organic layer was separated and then washed with a saturated solution of NaHCO3 (2×100 mL) and water (80 mL), dried over sodium sulfate, filtered, and concentered in vacuo to give 1.061 g of (46%) of the title compound as a pale brown solid.

Workup

  1. temperaturethe mixture was then refluxed for 3 hours
  2. temperatureThe reaction mixture was cooled
  3. stirringvigorously stirred for 2 hours
  4. customOrganic layer was separated
  5. washwashed with a saturated solution of NaHCO3 (2×100 mL) and water (80 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered

Sources & evidence

ORD record
ord-d97e8d0e68ea4814af704f3f64b1e5ed
Source dataset
uspto-grants-2014_07
Patent number
US08772280B2

Reaction notes

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