Potassium Carbonate → HCID 18459338, compound

HRID 382920Notes

Reaction equation

HRID 382920 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[CH:31]=[CH:30][C:14]([O:15][C:16]2[C:21]([F:22])=[C:20](F)[C:19]([F:24])=[C:18]([F:25])[C:17]=2[C:26]([F:29])([F:28])[F:27])=[CH:13][CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:32]([C:35]1[CH:41]=[CH:40][C:38]([O-:39])=[CH:37][C:36]=1[O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([O-:34])=[O:33].[K+].C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[K+]>CS(C)=O>[N+:32]([C:35]1[CH:41]=[CH:40][C:38]([O:39][C:20]2[C:19]([F:24])=[C:18]([F:25])[C:17]([C:26]([F:27])([F:28])[F:29])=[C:16]([O:15][C:14]3[CH:13]=[CH:12][C:11]([C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[O:10])=[CH:31][CH:30]=3)[C:21]=2[F:22])=[CH:37][C:36]=1[O:42][CH2:43][C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)([O-:34])=[O:33]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 516893Potassium BicarbonateHCID 11781031Potassium 4-nitro-3-benzyloxyphenoxideHCID 184593362-(4-Benzyloxycarbonylphenoxy)-1-trifluoromethyl-3,4,5,6-tetrafluorobenzene

Product 1

HCID 18459338HCID 18459338, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

40 g of the 2-(4-benzyloxycarbonylphenoxy)-1-trifluoromethyl-3,4,5,6-tetrafluorobenzene (0.09 mol) prepared as described in Example 9 and 25.5 g of potassium 4-nitro-3-benzyloxyphenoxide (0.09 mol) are dissolved in 400 ml of dimethyl sulfoxide. 30 g of potassium carbonate (0.22 mol) are added in portions to the solution. The mixture is then stirred at room temperature for 24 hours and then heated at 60° C. for 24 hours, and 15 g of potassium hydrogencarbonate (0.15 mol) are then added. The reaction solution is then allowed to cool to room temperature and is filtered through a fluted filter. The crude product is extracted by shaking with 300 ml of ethyl acetate and 700 ml of water, and the organic phase is washed three times with water and evaporated in a rotary evaporator until the reaction product precipitates out. The reaction product is then recrystallized from a mixture of ethyl acetate and n-hexane (volume ratio 1:1) and then dried for 48 hours,under nitrogen at 40° C./10 mbar in a vacuum drying cabinet (yield: 94%).

Workup

  1. temperatureheated at 60° C. for 24 hours
  2. temperatureto cool to room temperature
  3. filtrationis filtered through
  4. filtrationa fluted filter
  5. extractionThe crude product is extracted
  6. stirringby shaking with 300 ml of ethyl acetate and 700 ml of water
  7. washthe organic phase is washed three times with water
  8. customevaporated in a rotary evaporator until the reaction product
  9. customprecipitates out
  10. customThe reaction product is then recrystallized from a mixture of ethyl acetate and n-hexane (volume ratio 1:1)
  11. customdried for 48 hours,under nitrogen at 40° C./10 mbar in a vacuum
  12. customdrying cabinet (yield: 94%)

Sources & evidence

ORD record
ord-db7e778c4dcf4d228e143bedc8a86bef
Source dataset
uspto-grants-2001_10
Patent number
US06310238B1

Reaction notes

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