Potassium Carbonate → 1-(3-Hydroxy-4-nitro-2,5,6-trifluorophenoxy)-3-benzyloxy-4-nitrobenzene

HRID 430056Notes

Reaction equation

HRID 430056 reaction equation
[N+:1]([C:4]1[C:27]([F:28])=[C:26]([F:29])[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[C:11]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:10]=2)=[C:6]([F:30])[C:5]=1F)([O-:3])=[O:2].C(=O)([O-])[O-:33].[K+].[K+].C(=O)([O-])O.[K+]>CS(C)=O.O>[OH:33][C:5]1[C:6]([F:30])=[C:7]([C:26]([F:29])=[C:27]([F:28])[C:4]=1[N+:1]([O-:3])=[O:2])[O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[C:11]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:10]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 516893Potassium BicarbonateHCID 183538401-(4-Nitro-2,3,5,6-tetrafluorophenoxy)-3-benzyloxy-4-nitrobenzene

Product 1

HCID 183538411-(3-Hydroxy-4-nitro-2,5,6-trifluorophenoxy)-3-benzyloxy-4-nitrobenzene

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

43.8 g of 1-(4-nitro-2,3,5,6-tetrafluorophenoxy)-3-benzyloxy-4-nitrobenzene prepared as described in Example 12 (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-b8ff8d57bf57473b9d6a1b89e3c21e49
Source dataset
uspto-grants-2001_11
Patent number
US06320081B1

Reaction notes

Loading…