Potassium Carbonate → 1-(4-Nitro-2,3,5,6-tetrafluorophenoxy)-3-(prop-2-enyloxy)-4-nitro-2,5,6-trifluorobenzene

HRID 430052Notes

Reaction equation

HRID 430052 reaction equation
[CH2:1]([O:4][C:5]1[C:6]([F:17])=[C:7]([OH:16])[C:8]([F:15])=[C:9]([F:14])[C:10]=1[N+:11]([O-:13])=[O:12])[CH:2]=[CH2:3].[F:18][C:19]1[C:24]([N+:25]([O-:27])=[O:26])=[C:23]([F:28])[C:22]([F:29])=[C:21](F)[C:20]=1[F:31].C(=O)([O-])[O-].[K+].[K+]>C1(=O)OCCC1>[N+:25]([C:24]1[C:23]([F:28])=[C:22]([F:29])[C:21]([O:16][C:7]2[C:8]([F:15])=[C:9]([F:14])[C:10]([N+:11]([O-:13])=[O:12])=[C:5]([O:4][CH2:1][CH:2]=[CH2:3])[C:6]=2[F:17])=[C:20]([F:31])[C:19]=1[F:18])([O-:27])=[O:26]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70154PentafluoronitrobenzeneHCID 183538423-(Prop-2-enyloxy)-4-nitro-2,5,6-trifluorophenol

Product 1

HCID 183538381-(4-Nitro-2,3,5,6-tetrafluorophenoxy)-3-(prop-2-enyloxy)-4-nitro-2,5,6-trifluorobenzene

Reagents, catalysts & solvents 1

HCID 7302Gamma-ButyrolactoneSolvent

Procedure

24.9 g of 3-(prop-2-enyloxy)-4-nitro-2,5,6-trifluorophenol prepared as described in Example 6 (0.1 mol) and 21.3 g of pentafluoronitrobenzene (0.1 mol) are dissolved in 300 ml of 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 precipitated crude 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 precipitated crude product
  10. customis then recrystallized from a mixture of methylene chloride and petrol ether (volume ratio 1:1)
  11. customdried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum
  12. customdrying cabinet

Sources & evidence

ORD record
ord-eb2af523c51045de8ebb774ae64d6b4b
Source dataset
uspto-grants-2001_11
Patent number
US06320081B1

Reaction notes

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