3,4-Dibromothiophene → 3,4-Bis(trimethylsilylethynyl)thiophene

HRID 420835Notes

Reaction equation

HRID 420835 reaction equation
Br[C:2]1[C:6](Br)=[CH:5][S:4][CH:3]=1.[CH3:8][Si:9]([C:12]#[CH:13])([CH3:11])[CH3:10].O1[CH2:18][CH2:17]CC1.C(NC(C)C)(C)C>[Cu](I)I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:8][Si:9]([C:12]#[C:13][C:2]1[C:6]([C:17]#[C:18][Si:9]([CH3:11])([CH3:10])[CH3:8])=[CH:5][S:4][CH:3]=1)([CH3:11])[CH3:10]

Participants

6

Reactant 3

HCID 184523,4-DibromothiopheneHCID 66111TrimethylsilylacetyleneHCID 18968793THF diisopropylamine

Product 1

HCID 576816483,4-Bis(trimethylsilylethynyl)thiophene

Reagents, catalysts & solvents 2

HCID 11776TriphenylphosphineCatalystHCID 83717Copper iodideCatalyst

Conditions

Temperature
70 °C

Procedure

2.5 ml (22.6 mmol) of 3,4-dibromothiophene, commercially available from Aldrich under the Product No. 24,715-4, and 8 ml (56.5 mmol) of trimethylsilylacetylene were mixed with a solvent of tetrahydrofuran/diisopropylamine (1:1), and 0.15 g (0.23 mmol) of palladium dichlorodiphosphine, 21 mg (0.11 mmol) of copper iodide and 0.1 g (0.36 mmol) of triphenylphosphine were then sequentially added thereto. The reaction solution was heated at 70° C. for 8 hours, and washed with an aqueous solution of ammonium chloride. The resulting organic layer was dried over magnesium sulfate, dried under reduced pressure, and purified using silica gel column chromatography, thus obtaining 1.5 g of 3,4-bis(trimethylsilylethynyl)thiophene (IIa).

Workup

  1. additionwere then sequentially added
  2. washwashed with an aqueous solution of ammonium chloride
  3. dry with materialThe resulting organic layer was dried over magnesium sulfate
  4. customdried under reduced pressure
  5. custompurified

Sources & evidence

ORD record
ord-d12e9b942f61492b9e1d970331ec83a6
Source dataset
uspto-grants-2012_01
Patent number
US08097694B2

Reaction notes

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