Pentafluoropyridine → 2-(4-Benzyloxycarbonylphenoxy)-3,4,5,6-tetrafluoropyridine

HRID 2304999Notes

Reaction equation

HRID 2304999 reaction equation
F[C:2]1[N:7]=[C:6]([F:8])[C:5]([F:9])=[C:4]([F:10])[C:3]=1[F:11].[CH2:12]([O:19][C:20]([C:22]1[CH:28]=[CH:27][C:25]([O-:26])=[CH:24][CH:23]=1)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[K+].[K]>CN(C)C=O>[CH2:12]([O:19][C:20]([C:22]1[CH:23]=[CH:24][C:25]([O:26][C:2]2[C:3]([F:11])=[C:4]([F:10])[C:5]([F:9])=[C:6]([F:8])[N:7]=2)=[CH:27][CH:28]=1)=[O:21])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 69690PentafluoropyridineHCID 5462222PotassiumHCID 23672351Potassium 4-benzyloxycarbonylphenoxide

Product 1

HCID 184593372-(4-Benzyloxycarbonylphenoxy)-3,4,5,6-tetrafluoropyridineYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

33.8 g of pentafluoropyridine (0.2 mol) are dissolved in 500 ml of dimethylformamide, the solution is cooled to OC by means of a cryostat, and a solution of 53.3 g of potassium 4-benzyloxycarbonylphenoxide (0.2 mol) in 400 ml of dimethylformamide is then added dropwise over the course of 2 hours. After 24 hours at 0° C., the potassium salt has reacted. The dimethylformamide is then removed in a rotary evaporator, the residue is taken up in a little tetrahydrofuran, and the solution is filtered through a silica-gel column. The clear solution obtained is evaporated in a rotary evaporator until the reaction product precipitates out. The reaction product is then stirred in n-hexane, filtered off via a fluted filter and then dried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum drying cabinet (yield: 91%).

Workup

  1. temperaturethe solution is cooled to OC by means of a cryostat
  2. customThe dimethylformamide is then removed in a rotary evaporator
  3. filtrationthe solution is filtered through a silica-gel column
  4. customThe clear solution obtained
  5. customis evaporated in a rotary evaporator until the reaction product
  6. customprecipitates out
  7. filtrationfiltered off via
  8. filtrationa fluted filter
  9. customdried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum
  10. customdrying cabinet (yield: 91%)

Sources & evidence

ORD record
ord-ac4e88d649814939b7b5b9123e4f502e
Source dataset
uspto-grants-2002_08
Patent number
US06437178B2

Reaction notes

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