1-Benzyloxy-4-nitro-2,3,5,6-tetrafluorobenzene → 1-Benzyloxy-3-(prop-2-enyloxy)-4-nitro-2,5,6-trifluorobenzene

HRID 430049Notes

Reaction equation

HRID 430049 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([F:15])=[C:13](F)[C:12]([N+:17]([O-:19])=[O:18])=[C:11]([F:20])[C:10]=1[F:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22]([O-:25])[CH:23]=[CH2:24].[Na+]>C(#N)C>[CH2:1]([O:8][C:9]1[C:10]([F:21])=[C:11]([F:20])[C:12]([N+:17]([O-:19])=[O:18])=[C:13]([O:25][CH2:22][CH:23]=[CH2:24])[C:14]=1[F:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 106856651-Benzyloxy-4-nitro-2,3,5,6-tetrafluorobenzeneHCID 23669913Sodium prop-2-enolate

Product 1

HCID 183538391-Benzyloxy-3-(prop-2-enyloxy)-4-nitro-2,5,6-trifluorobenzene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

30.1 g of the 1-benzyloxy-4-nitro-2,3,5,6-tetra-fluorobenzene prepared as described in Example 4 (0.1 mol) are dissolved in 250 ml of dry acetonitrile in a three-neck flask fitted with reflux condenser and stirrer, and 8 g of sodium prop-2-enolate (0.1 mol) are added in portions to the solution. The reaction mixture is stirred at room temperature for 1 hour and then refluxed for 24 hours. The reaction solution is then filtered via a fluted filter, and the crude product is extracted by shaking with 150 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 reaction product is then recrystallized from a mixture of n-hexane and methylene chloride (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. temperaturerefluxed for 24 hours
  4. filtrationThe reaction solution is then filtered via
  5. filtrationa fluted filter
  6. extractionthe crude product is extracted
  7. stirringby shaking with 150 ml of ethyl acetate and 300 ml of water
  8. washThe organic phase is washed three times with water
  9. dry with materialdried over sodium sulfate
  10. customevaporated to half in a rotary evaporator
  11. customThe precipitated reaction product
  12. customis then recrystallized from a mixture of n-hexane and methylene chloride (volume ratio 1:1)
  13. customdried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum
  14. customdrying cabinet

Sources & evidence

ORD record
ord-a8a79b53d8a1405d98abcc3a84e0ee78
Source dataset
uspto-grants-2001_11
Patent number
US06320081B1

Reaction notes

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