Nitric Acid → 3-Chloro-2-(4-fluoro-3-nitrophenyl)-5-(trifluoromethyl)pyridine

HRID 1276077Notes

Reaction equation

[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[C:7]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[N:8][CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1>S(=O)(=O)(O)O>[Cl:5][C:6]1[C:7]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[C:18]([N+:1]([O-:4])=[O:2])[CH:17]=2)=[N:8][CH:9]=[C:10]([C:12]([F:14])([F:15])[F:13])[CH:11]=1

Participants

Conditions

Temperature: 2.5 °C

Procedure

40.8 g of 100% nitric acid were added dropwise at from 0 to 5° C. to a solution of 118.9 g of 3-chloro-2-(4-fluorophenyl)-5-trifluoromethylpyridine in 563 ml of 96% sulfuric acid, and the mixture was then stirred at from 0 to 5° C. for 11/2 hours. For work-up, the reaction mixture was poured into 2 l of ice water, and the product was then extracted with ethyl acetate (3×300 ml). The combined organic phases were washed twice with 100 ml of water in each case, dried over sodium sulfate and then evaporated. Yield: 134.5 g (97%) of a colorless oil which crystallized slowly.

Workup

extractionthe product was then extracted with ethyl acetate (3×300 ml)
washThe combined organic phases were washed twice with 100 ml of water in each case
dry with materialdried over sodium sulfate
customevaporated
customYield: 134.5 g (97%) of a colorless oil which crystallized slowly

Sources & evidence

ORD record: ord-19afcbb84c9f47549b8ecc0cbbd32682
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06165941

Reaction notes

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