Phosphorus oxychloride → 2-Chloro-4-(4-fluorobenzoyl)-pyridine

HRID 65532Notes

Reaction equation

HRID 65532 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][N+:11]([O-])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:19]>>[Cl:19][C:12]1[CH:13]=[C:8]([C:6](=[O:7])[C:5]2[CH:15]=[CH:16][C:2]([F:1])=[CH:3][CH:4]=2)[CH:9]=[CH:10][N:11]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 541432034-(4-fluorobenzoyl)-pyridine N-oxide

Product 1

HCID 201457102-Chloro-4-(4-fluorobenzoyl)-pyridine

Procedure

0.88 g 4-(4-fluorobenzoyl)-pyridine N-oxide and 50 ml POCl3 are refluxed for 2 hrs. Excess POCl3 is distilled at normal pressure. The crude is treated with slightly alkaline cold water and then extracted with methylene chloride. Working as usual affords 0.80 g of title product, identical with that obtained by the Friedel-Crafts process (see Ex. 3d).

Workup

  1. distillationExcess POCl3 is distilled at normal pressure
  2. additionThe crude is treated with slightly alkaline cold water
  3. extractionextracted with methylene chloride

Sources & evidence

ORD record
ord-b36102e79113467b91a9a346fad3538f
Source dataset
uspto-grants-1986_09
Patent number
US04614833

Reaction notes

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