Diethyl Ether → HCID 86626222, compound

HRID 554066Notes

Reaction equation

HRID 554066 reaction equation
[C:1]([OH:5])([CH3:4])([CH3:3])C.[C:6]([CH2:9][C:10](=[O:12])[CH3:11])(=[O:8])[CH3:7].Br[CH2:14][C:15]1[C:20]([F:21])=[C:19]([F:22])[C:18]([F:23])=[C:17]([CH2:24]Br)[C:16]=1[F:26].[I-].[K+].[CH2:29]([O:31]CC)[CH3:30]>O>[F:26][C:16]1[C:15]([CH2:14][CH:9]([C:10](=[O:12])[CH3:11])[C:6](=[O:8])[CH3:7])=[C:20]([F:21])[C:19]([F:22])=[C:18]([F:23])[C:17]=1[CH2:24][CH:3]([C:29](=[O:31])[CH3:30])[C:1](=[O:5])[CH3:4]

Participants

7

Reactant 5

HCID 3283Diethyl EtherHCID 4875Potassium IodideHCID 6386tert-ButanolHCID 31261AcetylacetoneHCID 86626223HCID 86626223, compound

Product 1

HCID 86626222HCID 86626222, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
82 °C

Procedure

In a four-neck flask, 6.66 g (59.4 mmol) of t-butokypotassium and 128 mL of t-butylalcohol were put in, agitated at a temperature of 82° C. for 30 minutes, dropped with 9.01 g (89.1 mmol) of acetylacetone for 12 minutes at the temperature, and then agitated for 2 hours. Thereafter, at 83° C., 12.8 g (purity 78.0%, 29.7 mmol) of 1,3-bis(bromomethyl)-2,4,5,6-tetrafluorobenzene was added for 25 minutes, and then agitated for 1 hour. Thereafter, 1.18 g (7.13 mmol) of potassium iodide was added at 82° C., and then agitated for 2 hours. After the solution was cooled down to a room temperature, it was added with 200 mL of diethylether, and 300 mL of water to be subjected to an extraction operation, and then an organic layer was separated from a water layer. The organic layer obtained was added with 300 mL of saturated aqueous salt solution and agitated, and then an organic layer was separated from a water layer, dried with anhydrous sodium sulfate, concentrated by distilling off the solvent, and then purified with silica gel column chromatography to obtain 7.2 g of a crude product. 4.66 g of the crude product obtained was re-crystallized with a mixed solvent of hexane and ethylacetate to obtain 1.46 g (yield 20%) of 3,3′-[2,4,5,6-tetrafluoro-1,3-phenylenebis(methylene)]bis(2,4-pentanedione)

Workup

  1. stirringagitated for 2 hours
  2. stirringagitated for 1 hour
  3. stirringagitated for 2 hours
  4. temperatureAfter the solution was cooled down to a room temperature
  5. customan organic layer was separated from a water layer
  6. customThe organic layer obtained
  7. stirringagitated
  8. customan organic layer was separated from a water layer
  9. dry with materialdried with anhydrous sodium sulfate
  10. concentrationconcentrated
  11. distillationby distilling off the solvent
  12. custompurified with silica gel column chromatography
  13. customto obtain 7.2 g of a crude product
  14. custom4.66 g of the crude product obtained
  15. customwas re-crystallized with a mixed solvent of hexane and ethylacetate

Sources & evidence

ORD record
ord-433d34031e454f6a8d37fce0e19be883
Source dataset
uspto-grants-2011_11
Patent number
US08048982B2

Reaction notes

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