Trichloroacetyl chloride → 5-(p-Chlorophenyl)pyrrol-5-yl trichloromethyl ketone

HRID 129631Notes

Reaction equation

HRID 129631 reaction equation
[Cl:1][C:2]([Cl:7])([Cl:6])[C:3](Cl)=[O:4].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[NH:16][CH:17]=[CH:18][CH:19]=2)=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>CCOCC.C(OCC)(=O)C>[Cl:1][C:2]([C:3]([C:15]1([C:12]2[CH:13]=[CH:14][C:9]([Cl:8])=[CH:10][CH:11]=2)[N:16]=[CH:17][CH:18]=[CH:19]1)=[O:4])([Cl:7])[Cl:6]

Participants

6

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 11430Potassium CarbonateHCID 2724282-(4-Chlorophenyl)-1h-pyrrole

Product 1

HCID 189303945-(p-Chlorophenyl)pyrrol-5-yl trichloromethyl ketoneYield 77.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of trichloroacetyl chloride (11.26 g, 0.0619 mol) in ether is treated with a solution of 2-(p-chlorophenyl)pyrrole (10.0 g, 0.0503 mol) in ether, stirred for four hours at room temperature, treated with saturated potassium carbonate solution and diluted with ethyl acetate. The organic phase is separated, washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a yellow solid. The solid is recrystallized from 2-propanol to give the title product as a yellow solid (12.63 g, mp 166°-168° C.) which is identified by 1HNMR spectral analysis.

Workup

  1. customThe organic phase is separated
  2. washwashed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto obtain a yellow solid
  6. customThe solid is recrystallized from 2-propanol

Sources & evidence

ORD record
ord-dff9a2e854e94541aee884d3fb28c0dd
Source dataset
uspto-grants-1995_11
Patent number
US05468877

Reaction notes

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