1,2-Diiodobenzene → Silane, [(2-iodophenyl)ethynyl]trimethyl-

HRID 2055834Notes

Reaction equation

HRID 2055834 reaction equation
C(C1C=CC=CC=1C#N)#C.[CH3:11][Si:12]([C:15]#[CH:16])([CH3:14])[CH3:13].[I:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1I>[Pd]>[CH3:11][Si:12]([CH3:14])([CH3:13])[C:15]#[C:16][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[I:17]

Participants

5

Reactant 3

HCID 119941,2-DiiodobenzeneHCID 66111TrimethylsilylacetyleneHCID 111160742-ethynylbenzonitrile

Product 1

HCID 10979486Silane, [(2-iodophenyl)ethynyl]trimethyl-Yield 58%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Alternatively, 2-ethynylbenzonitrile (a3) may be prepared according to the procedures set forth in M. J. Wu et al. (1999), Organic Letters, 1 (5):767-768, which is incorporated herein by reference in its entirety. Specifically, palladium-catalyzed coupling reaction of trimethylsilylacetylene with 1,2-diiodobenzene produced 2-(2-trimethylsilylethynyl)iodobenzene in 58% yield; 2-(2-trimethylsilylethynyl)iodobenzene was then coupled with Zn(CN)2 using palladium(0) as a catalyst to give 2-(2-trimethylsilylethynyl)benzonitrile in 45% yield; and finally, 2-(2-trimethylsilylethynyl)benzonitrile was treated with tetrabutylammonium fluoride to give 2-ethynylbenzonitrile (a3) in 97% yield.

Sources & evidence

ORD record
ord-d1659a2ff2b74f748dbd6e70291b27a0
Source dataset
uspto-grants-2008_02
Patent number
US07332623B2

Reaction notes

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