Water → 3-Ethyl 5-methyl 6-(difluoromethyl)-4-fluoro-2-(trifluoromethyl)-3,5-pyridinedicarboxylate

HRID 2291501Notes

Reaction equation

HRID 2291501 reaction equation
[F-:1].[K+].[F:3][CH:4]([F:25])[C:5]1[N:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:7](Cl)[C:6]=1[C:21]([O:23][CH3:24])=[O:22].O>CC#N.C1OCCOCCOCCOCCOCCOC1>[F:3][CH:4]([F:25])[C:5]1[N:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:7]([F:1])[C:6]=1[C:21]([O:23][CH3:24])=[O:22]

Participants

6

Reactant 3

HCID 962WaterHCID 522689Potassium FluorideHCID 140137713-Ethyl 5-methyl 6-(difluoromethyl)-4-chloro-2-(trifluoromethyl)-3,5-pyridinedicarboxylate

Product 1

HCID 140137723-Ethyl 5-methyl 6-(difluoromethyl)-4-fluoro-2-(trifluoromethyl)-3,5-pyridinedicarboxylateYield 97.8%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6342AcetonitrileSolvent

Procedure

The reagent was prepared by dissolving 0.37 g (0.001 mol) of 18-crown-6 in 30 ml of dry CH3CN (distilled over CaH2) and then adding 3.25 g (0.056 mol) of dry KF (dried in an oven at 50° C./67 Pa). After the heterogeneous system was mechanically stirred for 30 minutes, 10 g (0.028 mol) of product of Example 103 was added and the resulting mixture was refluxed for 6 days. The reaction mixture was poured into H2O, extracted with diethyl ether (2×), dried (MgSO4) and solvent removed in vacuo affording 9.45 g of a brown oil. The crude product was purified by HPLC using 1% ethyl acetate/cyclohexane as eluting solvent affording 6.72 g (70%) of product as a white solid; mp 40°-41° C.

Workup

  1. customThe reagent was prepared
  2. temperaturethe resulting mixture was refluxed for 6 days
  3. extractionextracted with diethyl ether (2×)
  4. dry with materialdried (MgSO4) and solvent
  5. customremoved in vacuo

Sources & evidence

ORD record
ord-951da8c55009413a98d1973302a3490d
Source dataset
uspto-grants-1989_01
Patent number
US04797149

Reaction notes

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