Benzyl Alcohol → 1-Benzyloxy-4-nitro-2,3,5,6-tetrafluorobenzene

HRID 430048Notes

Reaction equation

HRID 430048 reaction equation
[F:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([F:11])[C:5]([F:12])=[C:4](F)[C:3]=1[F:14].[CH2:15]([OH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>C1(=O)OCCC1>[CH2:15]([O:22][C:4]1[C:5]([F:12])=[C:6]([F:11])[C:7]([N+:8]([O-:10])=[O:9])=[C:2]([F:1])[C:3]=1[F:14])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 11430Potassium CarbonateHCID 70154Pentafluoronitrobenzene

Product 1

HCID 106856651-Benzyloxy-4-nitro-2,3,5,6-tetrafluorobenzene

Reagents, catalysts & solvents 1

HCID 7302Gamma-ButyrolactoneSolvent

Procedure

21.3 g of pentafluoronitrobenzene (0.1 mol) and 12 g of benzyl alcohol (0.11 mol, i.e. a 10% excess) are dissolved in 200 ml of dry γ-butyrolactone in a three-neck flask fitted with stirrer. 30 g of potassium carbonate (0.22 mol) are then added in portions, and the mixture is stirred at room temperature for 24 hours. The reaction solution is then filtered via a fluted filter, and the crude product is extracted by shaking with 200 ml of ethyl acetate and 300 ml of water. The organic phase is washed three times with water, dried over sodium sulfate and evaporated to half in a rotary evaporator. The reaction product crystallizes from the initially viscous solution. The precipitated reaction product is then recrystallized from a mixture of methylene chloride and petrol ether (volume ratio 1:1) and then dried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum drying cabinet.

Workup

  1. customfitted with stirrer
  2. filtrationThe reaction solution is then filtered via
  3. filtrationa fluted filter
  4. extractionthe crude product is extracted
  5. stirringby shaking with 200 ml of ethyl acetate and 300 ml of water
  6. washThe organic phase is washed three times with water
  7. dry with materialdried over sodium sulfate
  8. customevaporated to half in a rotary evaporator
  9. customThe reaction product crystallizes from the initially viscous solution
  10. customThe precipitated reaction product
  11. customis then recrystallized from a mixture of methylene chloride and petrol ether (volume ratio 1:1)
  12. customdried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum
  13. customdrying cabinet

Sources & evidence

ORD record
ord-608e230a59394381841ef2acc7122529
Source dataset
uspto-grants-2001_11
Patent number
US06320081B1

Reaction notes

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