Tetrahydrofuran → 1-bromo-4-(phenylethynyl)benzene

HRID 642913Notes

Reaction equation

HRID 642913 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[C:9]1([C:15]#[CH:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O1CCCC1>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I.C(N(CC)CC)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:16]#[C:15][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 8028TetrahydrofuranHCID 10821PhenylacetyleneHCID 115221-Bromo-4-iodobenzene

Product 1

HCID 2908881-bromo-4-(phenylethynyl)benzeneYield 58.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolvent

Procedure

28.3 g (0.10 mol) of p-bromoiodobenzene, 10.2 g (0.10 mol) of phenylacetylene, 701 mg (1 mmol) of bis(triphenylphosphine)palladium(II)dichloride, and 190 mg (1 mmol) of copper (I) iodide were placed in a 1000-mL three-neck flask, and nitrogen substitution was carried out. Then, 350 mL of tetrahydrofuran and 18 mL of triethylamine were added thereto, and the mixture was stirred at room temperature for 12 hours. After the reaction, the reaction mixture washed with a 3% hydrochloric acid aqueous solution, and the aqueous phase was extracted with ethyl acetate. The extracted solution combined with the organic phase washed with brine and dried with magnesium sulfate. The mixture was filtered through celite, florisil, and alumina, and a solid obtained by the concentration of the filtrate was recrystallized with hexane to give 15 g of a solid that was the target substrate in the yield of 58%.

Workup

  1. customAfter the reaction
  2. washthe reaction mixture washed with a 3% hydrochloric acid aqueous solution
  3. extractionthe aqueous phase was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried with magnesium sulfate
  6. filtrationThe mixture was filtered through celite, florisil, and alumina
  7. customa solid obtained by the concentration of the filtrate
  8. customwas recrystallized with hexane

Sources & evidence

ORD record
ord-54a909303b374952a064f6f8bd93760e
Source dataset
uspto-grants-2010_04
Patent number
US07696348B2

Reaction notes

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