Water → HCID 53670716, compound

HRID 2052762Notes

Reaction equation

HRID 2052762 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[C:4]([F:9])[CH:3]=1.[CH:10]#[C:11][CH2:12][CH2:13][CH3:14].O.CCOCC>C1COCC1.C(N(CC)CC)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:10]#[C:11][CH2:12][CH2:13][CH3:14])=[C:4]([F:9])[CH:3]=1

Participants

9

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 123091-PentyneHCID 27245164-Bromo-2-fluoro-1-iodobenzene

Product 1

HCID 53670716HCID 53670716, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
10 °C

Procedure

190 g (0.600 mol) of 4-bromo-2-fluoro-1-iodobenzene and 65.3 ml of 1-pentyne were dissolved in a mixture of 900 ml of THF and 1.2 l of triethylamine and cooled to 10° C., and 1.14 g (6 mmol) of copper(I) iodide and 8.42 g (12 mmol) of bis(triphenylphosphine)palladium(II) chloride were added. The batch was stirred overnight at room temperature, water and MTB ether were subsequently added, and the mixture was stirred for a further 5 minutes. The reaction mixture was filtered through Celite® with suction, and the phases were separated. The aqueous phase was extracted twice with MTB ether, and the combined organic phases were washed three times with water, dried over sodium sulfate and evaporated under reduced pressure. The crude product was filtered through silica gel with n-heptane, giving 129 g of 4-bromo-2-fluoro-1-pent-1-ynylbenzene as a yellow liquid. Hydrogenation on palladium/activated carbon (10%) in THF gave 131 g (100%) of 4-bromo-2-fluoro-1-pentylbenzene as a yellow liquid.

Workup

  1. stirringthe mixture was stirred for a further 5 minutes
  2. filtrationThe reaction mixture was filtered through Celite® with suction
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted twice with MTB ether
  5. washthe combined organic phases were washed three times with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated under reduced pressure
  8. filtrationThe crude product was filtered through silica gel with n-heptane

Sources & evidence

ORD record
ord-6335e2f2f40b4d0ba02708c43848d337
Source dataset
uspto-grants-2008_02
Patent number
US07326447B2

Reaction notes

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