Water → 1-(3-Hydroxy-4-nitro-2,5,6-trifluorophenoxy)-3-(prop-2-enyloxy)-4-nitro-2,5,6-trifluorobenzene

HRID 430053Notes

Reaction equation

HRID 430053 reaction equation
[N+:1]([C:4]1[C:26](F)=[C:25]([F:28])[C:7]([O:8][C:9]2[C:14]([F:15])=[C:13]([F:16])[C:12]([N+:17]([O-:19])=[O:18])=[C:11]([O:20][CH2:21][CH:22]=[CH2:23])[C:10]=2[F:24])=[C:6]([F:29])[C:5]=1[F:30])([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[K+].[OH2:42]>CS(C)=O>[OH:42][C:26]1[C:25]([F:28])=[C:7]([C:6]([F:29])=[C:5]([F:30])[C:4]=1[N+:1]([O-:3])=[O:2])[O:8][C:9]1[C:14]([F:15])=[C:13]([F:16])[C:12]([N+:17]([O-:19])=[O:18])=[C:11]([O:20][CH2:21][CH:22]=[CH2:23])[C:10]=1[F:24]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 516893Potassium BicarbonateHCID 183538381-(4-Nitro-2,3,5,6-tetrafluorophenoxy)-3-(prop-2-enyloxy)-4-nitro-2,5,6-trifluorobenzene

Product 1

HCID 183538371-(3-Hydroxy-4-nitro-2,5,6-trifluorophenoxy)-3-(prop-2-enyloxy)-4-nitro-2,5,6-trifluorobenzene

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

44.2 g of 1-(4-nitro-2,3,5,6-tetrafluorophenoxy)-3-(prop-2-enyloxy)-4-nitro-2,5,6-trifluorobenzene prepared as described in Example 9 (0.1 mol) are dissolved in a mixture of 200 ml of dimethyl sulfoxide and 30 ml of water in a three-neck flask fitted with reflux condenser and stirrer. 15 g of potassium carbonate (0.11 mol) and 10 g of potassium hydrogen carbonate (0.1 mol) are added in portions to the solution, and the mixture is then stirred at 80° C. 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 400 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 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
  2. temperaturewith reflux condenser and stirrer
  3. filtrationThe reaction solution is then filtered via
  4. filtrationa fluted filter
  5. extractionthe crude product is extracted
  6. stirringby shaking with 200 ml of ethyl acetate and 400 ml of water
  7. washThe organic phase is washed three times with water
  8. dry with materialdried over sodium sulfate
  9. customevaporated to half in a rotary evaporator
  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-0ff855c9e1be4e2fa9d5e5ada65d89d0
Source dataset
uspto-grants-2001_11
Patent number
US06320081B1

Reaction notes

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