Butyl nitrite → HCID 13175418, compound

HRID 2164402Notes

Reaction equation

HRID 2164402 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](N)=[C:4]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:3]=1.N(OCCCC)=O.[H+].[F:24][P-](F)(F)(F)(F)F>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([F:24])=[C:4]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:3]=1

Participants

4

Reactant 3

HCID 10996Butyl nitriteHCID 13175417HCID 13175417, compoundHCID 16211447Hexafluorophosphoric acid

Product 1

HCID 13175418HCID 13175418, compound

Procedure

A diazonium salt is formed by reacting 2-chloro-5-amino- 6-phenoxypyridine with butyl nitrite in the presence of HPF6 and is decomposed by heating (Baltz-Schiemann reaction) to obtain 2-chloro-5-fluoro-6-phenoxypyridine. The obtained product is reacted with magnesium and then with a formylating agent such as dimethylformamide to obtain 5-fluoro-6-phenoxy picolinic aldehyde. In the case where cyano(5-fluoro-6-phenoxy-2-pyridyl) methyl alcohol is required, it is prepared by reacting the aldehyde with sodiumbisulfite and then with a cyanide compound such as sodium cyanide.

Workup

  1. temperatureby heating
  2. custom(Baltz-Schiemann reaction)

Sources & evidence

ORD record
ord-c1d38db6e91b450cb916cd2d3a2f5c21
Source dataset
uspto-grants-1985_03
Patent number
US04504483

Reaction notes

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