1-Bromo-4-fluorobenzene → p-Fluoropentylbenzene

HRID 2395418Notes

Reaction equation

HRID 2395418 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=C.[Mg].Br[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1>O1CCCC1.CCOCC.[Cl-].[Cl-].[Zn+2]>[F:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[CH:11][CH:12]=1

Participants

7

Reactant 3

HCID 99931-Bromo-4-fluorobenzeneHCID 759066-Bromo-1-hexeneHCID 5462224Magnesium2×

Product 1

HCID 2737448p-Fluoropentylbenzene

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 6-bromo-1-hexene (10 g), magnesium (1 .5g), and lodoethane (1 drop) in anhydrous tetrahydrofuran was heated at reflux until all of the magnesium dissolved. The resulting Grignard reagent was cooled to about 0° C. and was treated with a 1M solution of ZnCl2 in ether (67 ml), and the mixture was allowed to warm to room temperature over 30 minutes. Tetraids(triphenylphosphine)palladium (0) (3.5 g) and 4-bromofluorobenzene (6.73 ml) were added to the reaction and the mixture was heated to reflux for 1 hour. The mixture was cooled to room temperature, concentrated in vacuo, diluted with hexane, filtered and concentrated once more in vacuo. Chromatography on a silica gel column eluting with ether-hexane (0-5%) afforded 5 g of a colorless oil.

Workup

  1. temperaturewas heated
  2. dissolutiondissolved
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 1 hour
  5. temperatureThe mixture was cooled to room temperature
  6. concentrationconcentrated in vacuo
  7. additiondiluted with hexane
  8. filtrationfiltered
  9. concentrationconcentrated once more in vacuo
  10. washChromatography on a silica gel column eluting with ether-hexane (0-5%)

Sources & evidence

ORD record
ord-cb752c8c5282404c97ae76b18ebe3c7e
Source dataset
uspto-grants-1998_09
Patent number
US05814651

Reaction notes

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