Sodium Cyanide → 3-Chloro-5-(trifluoromethyl)pyridine-2-carbonitrile

HRID 897163Notes

Reaction equation

HRID 897163 reaction equation
[C-:1]#[N:2].[Na+].[Cl:4][C:5]1[C:6](F)=[N:7][CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:4][C:5]1[C:6]([C:1]#[N:2])=[N:7][CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 12680753-Chloro-2-fluoro-5-(trifluoromethyl)pyridine

Product 1

HCID 14733743-Chloro-5-(trifluoromethyl)pyridine-2-carbonitrileYield 82.1%

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

Solid sodium cyanide (0.29 g) was added to a stirred mixture of 3-chloro-2-fluoro-5-trifluoromethylpyridine (0.8 g) and tetrabutylammonium bromide (0.06 g) at 20-25° C., and stirred for 23 hours to give 3-chloro-2-cyano-5-trifluoromethylpyridine (0.68 g, 82% yield by hplc).

Sources & evidence

ORD record
ord-a2b6be94861e467ea99473efde87ab04
Source dataset
uspto-grants-2005_07
Patent number
US06921828B2

Reaction notes

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