Chlorine → 4'-Chloro-2'-fluoroacetanilide

HRID 1076920Notes

Reaction equation

HRID 1076920 reaction equation
[Cl:1]Cl.[F:3][C:4]1[CH:13]=[CH:12][CH:11]=[CH:10][C:5]=1[NH:6][C:7](=[O:9])[CH3:8]>C(O)(=O)C>[Cl:1][C:12]1[CH:11]=[CH:10][C:5]([NH:6][C:7](=[O:9])[CH3:8])=[C:4]([F:3])[CH:13]=1

Participants

4

Reactant 2

HCID 24526ChlorineHCID 67860N-(2-Fluorophenyl)acetamide

Product 1

HCID 8531744'-Chloro-2'-fluoroacetanilide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Seventy-one parts of liquid chlorine were added to a solution of 140 parts of 2'-fluoroacetanilide in 500 parts glacial acetic acid, during one hour, at 25°-27°C, with icewater cooling. While stirring for 4 hours at 25°-27°C, 4'-chloro-2'-fluoroacetanilide precipitated. After collecting the product by filtration, the filtrate was poured over 2000 parts of ice. The resulting second portion of precipitated product was collected by filtration, combined with the first portion and recrystallized from 700 parts of methanol at -45°C to yield 119 parts of 4'-chloro-2'-fluoroacetanilide as white crystals melting at 152°-155°C.

Workup

  1. temperaturecooling
  2. custom4'-chloro-2'-fluoroacetanilide precipitated
  3. customAfter collecting the product
  4. filtrationby filtration
  5. additionthe filtrate was poured over 2000 parts of ice
  6. filtrationThe resulting second portion of precipitated product was collected by filtration
  7. customrecrystallized from 700 parts of methanol at -45°C

Sources & evidence

ORD record
ord-77dfad2de8d049b7846f5ef1b3d80755
Source dataset
uspto-grants-1976_05
Patent number
US03958976

Reaction notes

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