Trimethylsilylacetylene → HCID 68649922, compound

HRID 634044Notes

Reaction equation

HRID 634044 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8](Br)=[C:7](Br)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:13]([Si:15]([CH3:18])([CH3:17])[CH3:16])#[CH:14]>[Cu](I)I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(N(CC)CC)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:14]#[C:13][Si:15]([CH3:18])([CH3:17])[CH3:16])=[C:7]([C:14]#[C:13][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 66111Trimethylsilylacetylene2×HCID 122508051,2-Dibromo-4-tert-butylbenzene

Product 1

HCID 68649922HCID 68649922, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

4-tert-butyl-1,2-dibromobenzene (5.0 g, 17 mmol), copper iodide (0.17 g, 0.9 mmol), tetrakis(triphenylphosphine)palladium (1.04 g, 0.9 mmol), ethynyltrimethylsilane (4.2 g, 43 mmol), and triethylamine (25 ml) were heated to 20° C. and stirred for 4 hours. The reaction mixture was then heated to 80° C. for 44 hours. Additional ethynyltrimethylsilane (2.5 g, 25 mmol) was added and the reaction mixture was stirred at 47° C. for 60 hours. Column chromatography (silica) was performed to remove metals and salts, using heptane as eluent. The crude product mixture was used without further purification.

Workup

  1. stirringthe reaction mixture was stirred at 47° C. for 60 hours
  2. customto remove metals and salts
  3. customThe crude product mixture was used without further purification

Sources & evidence

ORD record
ord-8f460d5941ad4e8e9d486b32047d687d
Source dataset
uspto-grants-2016_04
Patent number
US09321896B2

Reaction notes

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