Water → 2,5-Bis(perfluorobutyl)-p-xylene

HRID 643218Notes

Reaction equation

HRID 643218 reaction equation
[C:1](I)([C:4]([C:7]([C:10]([F:13])([F:12])[F:11])([F:9])[F:8])([F:6])[F:5])([F:3])[F:2].I[C:16]1[CH:21]=[C:20]([CH3:22])[C:19](I)=[CH:18][C:17]=1[CH3:24].ClCCl.O>CS(C)=O.[Cu]>[F:2][C:1]([F:3])([C:16]1[CH:21]=[C:20]([CH3:22])[C:19]([C:1]([F:3])([F:2])[C:4]([F:5])([F:6])[C:7]([F:8])([F:9])[C:10]([F:13])([F:12])[F:11])=[CH:18][C:17]=1[CH3:24])[C:4]([F:6])([F:5])[C:7]([F:9])([F:8])[C:10]([F:13])([F:12])[F:11]

Participants

7

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 67917Perfluorobutyl iodideHCID 27361711,4-Diiodo-2,5-dimethylbenzene

Product 1

HCID 591842082,5-Bis(perfluorobutyl)-p-xyleneYield 73%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of C4F9I (0.96 mL, 5.6 mmol) was added dropwise over 10 min to a stirred mixture of 2,5-diiodo-ρ-xylene (0.5 g, 1.4 mmol), copper powder (1.4 g, 22.4 mmol) in DMSO (10 mL) at 130° C. The reaction mixture was subsequently stirred for a further 24 h at this temperature. After cooling to room temperature, it was poured into a beaker containing dichloromethane (30 mL) and water (30 mL). After filtering, the organic layer was separated, washed with water (3×30 mL) and dried over MgSO4. The residue was purified by column chromatography (hexane as eluant) to give the product 8 as a white solid (553 mg, 73%).

Workup

  1. additionit was poured into a beaker
  2. filtrationAfter filtering
  3. customthe organic layer was separated
  4. washwashed with water (3×30 mL)
  5. dry with materialdried over MgSO4
  6. customThe residue was purified by column chromatography (hexane as eluant)

Sources & evidence

ORD record
ord-012af6c98ac14a1f84a7e6dac3d6f465
Source dataset
uspto-grants-2010_04
Patent number
US07700366B2

Reaction notes

Loading…