Oxygen → ((4-Bromophenyl)ethynyl)triisopropylsilane

HRID 2246489

Reaction equation

HRID 2246489 reaction equation
[CH:1]([Si:4]([C:11]#[CH:12])([CH:8]([CH3:10])[CH3:9])[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].C(N(CC)CC)C.O=O.[Br:22][C:23]1[CH:28]=[CH:27][C:26](I)=[CH:25][CH:24]=1>O1CCCC1.[Cu](I)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:22][C:23]1[CH:28]=[CH:27][C:26]([C:12]#[C:11][Si:4]([CH:5]([CH3:6])[CH3:7])([CH:1]([CH3:3])[CH3:2])[CH:8]([CH3:10])[CH3:9])=[CH:25][CH:24]=1

Participants

8

Reactant 4

HCID 977OxygenHCID 8471TriethylamineHCID 115221-Bromo-4-iodobenzeneHCID 2734682(Triisopropylsilyl)acetylene

Product 1

HCID 57809595((4-Bromophenyl)ethynyl)triisopropylsilane

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

11.6 mL triisopropylsilylacetylen and 14.4 mL triethylamine followed by 0.2 g copper iodide and 0.73 g bis-(triphenylphosphine)-palladium dichloride are added under argon to an oxygen-free solution of 15.0 g 4-bromo-1-iodo-benzene in 150 mL dry tetrahydrofuran. The solution is stirred for 16 h at ambient temperature and then filtered through Celite and evaporated down. The residue is purified by chromatography on silica gel (cyclohexane).

Workup

  1. filtrationfiltered through Celite
  2. customevaporated down
  3. customThe residue is purified by chromatography on silica gel (cyclohexane)

Sources & evidence

ORD record
ord-99738f654bff4a7da2cd2e1ca416f1a1
Source dataset
uspto-grants-2010_03
Patent number
US07687469B2

Linked notes

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