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

HRID 1975203Notes

Reaction equation

HRID 1975203 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-b18ff91ae9804eb0994d78a56d90179d
Source dataset
uspto-grants-1994_02
Patent number
US05284863

Reaction notes

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