Trifluoroacetic anhydride → HCID 90204252, compound

HRID 1480047Notes

Reaction equation

HRID 1480047 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=[O:4].[Br:14][C:15]1[C:16]([O:23][CH2:24][CH:25]2[CH2:27][CH2:26]2)=[CH:17][C:18]([CH3:22])=[N+:19]([O-])[CH:20]=1>ClCCl>[Br:14][C:15]1[C:16]([O:23][CH2:24][CH:25]2[CH2:27][CH2:26]2)=[CH:17][C:18]([CH2:22][OH:4])=[N:19][CH:20]=1

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 90203662HCID 90203662, compound

Product 1

HCID 90204252HCID 90204252, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic anhydride (24.4 g, 16.2 mL, 116 mmol) was added dropwise over a period of 10 min. to an ice cold solution of 5-bromo-4-(cyclopropylmethoxy)-2-methylpyridine 1-oxide (10.0 g, 38.7 mmol) in dichloromethane (100 mL). The ice bath was removed and the mixture was stirred at ambient temperature for 65 h. Under cooling 5.4N aqueous NaOH solution (50 mL) was added and the mixture was extracted with dichloromethane/methanol 9/1 (3×200 mL). The combined extracts were dried over Na2SO4, filtered and the filtrated was brought to dryness under reduced pressure. The residue was crystallized from ethyl acetate/heptane to yield the title compound (9 g, 90%) as brown solid; LC-MS (UV peak area, m/z) 99.5%, 258.0130 (MH+).

Workup

  1. customThe ice bath was removed
  2. temperatureUnder cooling 5.4N aqueous NaOH solution (50 mL)
  3. additionwas added
  4. extractionthe mixture was extracted with dichloromethane/methanol 9/1 (3×200 mL)
  5. dry with materialThe combined extracts were dried over Na2SO4
  6. filtrationfiltered
  7. customThe residue was crystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-b0cc6787545b4b5b8c989ca8eed1831b
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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