Hydrochloric Acid → 2-Chloroacetyl-1-(o-fluorophenethyl)pyrrole

HRID 2419576Notes

Reaction equation

HRID 2419576 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][CH:11]=[CH:10][C:3]=1[CH2:4]N1C=CC=C1.ClCC#N.Cl.[Cl:19][CH2:20][C:21]([C:23]1[N:24]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2F)[CH:25]=[CH:26][CH:27]=1)=[O:22]>CCOCC>[F:1][C:2]1[CH:13]=[CH:12][CH:11]=[CH:10][C:3]=1[CH2:4][CH2:21][C:23]1[NH:24][CH:25]=[CH:26][CH:27]=1.[Cl:19][CH2:20][C:21]([C:23]1[N:24]([CH2:28][CH2:29][C:34]2[CH:33]=[CH:32][CH:31]=[CH:30][C:2]=2[F:1])[CH:25]=[CH:26][CH:27]=1)=[O:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7856ChloroacetonitrileHCID 143914721-[(2-Fluorophenyl)methyl]-1H-pyrroleHCID 203915312-Chloro-1-{1-[(2-fluorophenyl)methyl]-1H-pyrrol-2-yl}ethan-1-one

Product 2

HCID 203915332-Chloroacetyl-1-(o-fluorophenethyl)pyrroleHCID 54477722o-Fluorophenethylpyrrole

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 40 g of 1-(o-fluorobenzyl)pyrrole and 17.2 g of chloroacetonitrile in 200 ml of anhydrous ether at a temperature between 0° and -5° C is saturated with hydrogen chloride gas and then the solution is stirred until a heavy white cake forms. This cake is broken up and permitted to sit for 1 hour at ambient temperature. The white solid is filtered, washed with ether and dried and then hydrolyzed in water and extracted with ether. Concentration of the ether extracts leaves white crystals, mp 76°-78° C, of 2-chloroacetyl-1-(o-fluorobenzyl)pyrrole. The analagous treatment of o-fluorophenethylpyrrole produces 2-chloroacetyl-1-(o-fluorophenethyl)pyrrole.

Workup

  1. customat a temperature between 0° and -5° C
  2. filtrationThe white solid is filtered
  3. washwashed with ether
  4. customdried
  5. extractionhydrolyzed in water and extracted with ether
  6. customConcentration of the ether extracts leaves white crystals, mp 76°-78° C

Sources & evidence

ORD record
ord-6adf59445a0948f187991614d7278122
Source dataset
uspto-grants-1978_08
Patent number
US04107187

Reaction notes

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