Chlorine → 4'-Chloro-2'-fluoroacetanilide

HRID 1729934Notes

Reaction equation

HRID 1729934 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[NH:4][C:5](=[O:7])[CH3:6].[Cl:12]Cl>C(O)(=O)C>[Cl:12][C:10]1[CH:9]=[CH:8][C:3]([NH:4][C:5](=[O:7])[CH3:6])=[C:2]([F:1])[CH:11]=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

A solution of 140 parts of 2'-fluoroacetanilide in 500 parts glacial acetic acid was treated with 71 parts of chlorine during 1 hour at 25°-27° C with ice-water 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 product pecipitated 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'-fluroacetanilide as white crystals melting at 152°-155° C.

Workup

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

Sources & evidence

ORD record
ord-0c95cdada44e48b4936d6eb2c2ea76ac
Source dataset
uspto-grants-1976_11
Patent number
US03990880

Reaction notes

Loading…