1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-6-iodohexane → HCID 102598921, compound

HRID 2176708Notes

Reaction equation

HRID 2176708 reaction equation
Br[C:2]1[C:3]2[C:8]([C:9](Br)=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[C:17](I)([C:20]([C:23]([C:26]([C:29]([C:32]([F:35])([F:34])[F:33])([F:31])[F:30])([F:28])[F:27])([F:25])[F:24])([F:22])[F:21])([F:19])[F:18]>CS(C)=O.[Cu]>[F:18][C:17]([F:19])([C:2]1[C:3]2[C:8]([C:9]([C:17]([F:19])([F:18])[C:20]([F:21])([F:22])[C:23]([F:24])([F:25])[C:26]([F:27])([F:28])[C:29]([F:31])([F:30])[C:32]([F:35])([F:34])[F:33])=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:20]([F:22])([F:21])[C:23]([F:25])([F:24])[C:26]([F:28])([F:27])[C:29]([F:31])([F:30])[C:32]([F:35])([F:34])[F:33]

Participants

5

Reactant 2

HCID 677331,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-6-iodohexaneHCID 682269,10-Dibromoanthracene

Product 1

HCID 102598921HCID 102598921, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

Under a nitrogen atmosphere, 9,10-dibromoanthracene (0.6 g, 1.78 mmol) and a copper powder (1.14 g, 17.8 mmol) were added to a 200 mL reaction vessel and were dissolved in anhydrous dimethyl sulfoxide (25 mL). α,α,α-Benzotrifluoride (25 mL) and C6F13I (1.96 mL, 8.93 mmol) were added thereto and reaction was carried out at 130° C. for 4 hours. After quenching with ice-water, the reaction solution was extracted with methylene chloride. Thereafter, the obtained organic layer was dried over anhydrous sodium sulfate and then filtrated. The filtrate was subjected to solvent removal on a rotary evaporator and, thereafter, separation and purification were conducted by using column chromatography. A 9,10-bis(perfluorohexyl)anthracene was obtained as a yellow solid.

Workup

  1. customreaction
  2. customAfter quenching with ice-water
  3. extractionthe reaction solution was extracted with methylene chloride
  4. dry with materialThereafter, the obtained organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltrated
  6. customThe filtrate was subjected to solvent removal on a rotary evaporator
  7. customseparation and purification

Sources & evidence

ORD record
ord-774624c2dc924d90bc485615de2dc96a
Source dataset
uspto-grants-2015_06
Patent number
US09067857B2

Reaction notes

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