1-Decyne → 2,5-Dibromo-3-decynylthiophene

HRID 646399Notes

Reaction equation

HRID 646399 reaction equation
[Br:1][C:2]1[S:3][C:4]([Br:8])=[CH:5][C:6]=1I.[CH:9]#[C:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>C(N(CC)CC)C.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.[Cu]I>[Br:1][C:2]1[S:3][C:4]([Br:8])=[CH:5][C:6]=1[C:9]#[C:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 2

HCID 129971-DecyneHCID 130111782,5-Dibromo-3-iodothiophene

Product 1

HCID 674601512,5-Dibromo-3-decynylthiophene

Reagents, catalysts & solvents 3

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

Conditions

Temperature
0 °C

Procedure

To a solution of the above prepared 2,5-dibromo-3-iodothiophene (3.43 grams, 9.3 mmol) and 1-decyne (1.45 grams, 10.5 mmol) in triethylamine (50 milliliters) were added dichlorobis(triphenylphosphine)palladium (II) (0.28 gram, 0.4 mmol) and copper(I) iodide (38 milligrams, 0.2 mmol) at 0° C. under argon. The reaction mixture was stirred at 0° C. for 6 hours and at room temperature for 20 hours under argon. After evaporation of the solvent, the product was purified by column chromatography on silica gel using hexane as eluent. 2,5-Dibromo-3-decynylthiophene was thus obtained as a colorless liquid was. Yield: 3.32 grams (94 percent).

Workup

  1. customAfter evaporation of the solvent
  2. customthe product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-3324ddc26b0145daac2f4891105257c5
Source dataset
uspto-grants-2010_04
Patent number
US07705111B2

Reaction notes

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