Trifluoroacetic anhydride → HCID 58431400, compound

HRID 1617395Notes

Reaction equation

HRID 1617395 reaction equation
[F:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].OO.NC(N)=[O:19].FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[C:10]([C:11]([F:14])([F:12])[F:13])=[N+:9]([O-:19])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 31294Carbamide PeroxideHCID 265964893-Fluoro-2-(trifluoromethyl)isonicotinic acid

Product 1

HCID 58431400HCID 58431400, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-fluoro-2-(trifluoromethyl)isonicotinic acid (2.00 g, 9.56 mmol, Oakwood) and urea hydrogen peroxide addition compound (5.00 g, 53.2 mmol, Aldrich) in methylene chloride (50 mL) at 0° C. was added trifluoroacetic anhydride (7.51 mL, 53.2 mmol). The bath was removed and the reaction was allowed to warm to room temperature and stir overnight. The precipitate was filtered off. The filtrate was diluted with a small amount of water and ethyl acetate, the layers were separated and the aqueous was extracted with two further portions of ethyl acetate. The combined extracts were dried over sodium sulfate, filtered and concentrated. The solvent was removed in vacuo to afford a yellow solid which was used without further purification. LC-MS: 225.9 (M+H)+. 1H NMR (300 MHz, CD3OD): δ 8.20 (d, 1H), 8.04 (dd, 1H).

Workup

  1. customThe bath was removed
  2. filtrationThe precipitate was filtered off
  3. additionThe filtrate was diluted with a small amount of water and ethyl acetate
  4. customthe layers were separated
  5. extractionthe aqueous was extracted with two further portions of ethyl acetate
  6. dry with materialThe combined extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe solvent was removed in vacuo
  10. customto afford a yellow solid which
  11. customwas used without further purification

Sources & evidence

ORD record
ord-0d36c39857bb43fda2213a25c09914a2
Source dataset
uspto-grants-2014_07
Patent number
US08765734B2

Reaction notes

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