Octafluorotoluene → 2-(4-Benzyloxycarbonylphenoxy)-1-trifluoromethyl-3,4,5,6-tetrafluorobenzene

HRID 2305002Notes

Reaction equation

HRID 2305002 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[C:8](F)=[C:7]([F:10])[C:6]([F:11])=[C:5]([F:12])[C:4]=1[F:13].[CH2:16]([O:23][C:24]([C:26]1[CH:32]=[CH:31][C:29]([O-:30])=[CH:28][CH:27]=1)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[K+].[K]>CN(C)C=O>[CH2:16]([O:23][C:24]([C:26]1[CH:27]=[CH:28][C:29]([O:30][C:8]2[C:7]([F:10])=[C:6]([F:11])[C:5]([F:12])=[C:4]([F:13])[C:3]=2[C:2]([F:1])([F:15])[F:14])=[CH:31][CH:32]=1)=[O:25])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 9906OctafluorotolueneHCID 5462222PotassiumHCID 23672351HCID 23672351, compound

Product 1

HCID 184593362-(4-Benzyloxycarbonylphenoxy)-1-trifluoromethyl-3,4,5,6-tetrafluorobenzeneYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

35.4 g of octafluorotoluene (0.15 mol) are dissolved in 400ml of dimethylformamide, the solution is cooled to 0øC using a cryostat, and a solution of 40 g of potassium 4-benzyloxycarbonylphenoxide (0.15 mol) in 300 ml of dimethylformamide is then added dropwise over the course of 2 hours. After 2hours 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 through a fluted filter and then dried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum drying cabinet (yield: 95%).

Workup

  1. temperaturethe solution is cooled to 0øC
  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 through
  8. filtrationa fluted filter
  9. customdried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum
  10. customdrying cabinet (yield: 95%)

Sources & evidence

ORD record
ord-32247d5b493a4b6cbd15b5f343d4136c
Source dataset
uspto-grants-2002_08
Patent number
US06437178B2

Reaction notes

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