1-Bromo-4-iodobenzene → 1-Bromo-4-(pentafluoroethyl)benzene

HRID 1755082Notes

Reaction equation

HRID 1755082 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.C[Si]([C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15])(C)C.[F-].[K+]>CN1CCCC1=O.[Cu](I)I>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 115221-Bromo-4-iodobenzeneHCID 522689Potassium FluorideHCID 2760820(Pentafluoroethyl)trimethylsilane

Product 1

HCID 542097081-Bromo-4-(pentafluoroethyl)benzeneYield 52%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 4-bromo-iodobenzene (500 mg, 1.77 mmol), trimethylsilylpentafluoroethane (679 mg, 3.53 mmol), copper iodide (672 mg, 3.53 mmol) and potassium fluoride (205 mg, 3.53 mmol) in N-methylpyrolidone (1.0 mL) was heated with stirring at 100° C. for three hours in a sealed reaction vessel. After cooling to room temperature, the reaction mixture was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to give 1-bromo-4-pentafluoroethylbenzene as a colorless liquid (253 mg, 52%).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was purified by silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-9f3bb198234b457cb4a57fdafe605a95
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

Loading…