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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 508752Generated: October 26, 2026

Trimethylsilylacetylene → 1,4-Dichloro-2-ethynylbenzene

https://huagongshe.com/reaction/508752

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrimethylsilylacetyleneHCID 66111—
Reactant1,4-Dichloro-2-iodobenzeneHCID 122452—
ReactantTetrabutylammonium FluorideHCID 2724141—
CatalystCopper iodideHCID 83717—
CatalystDichlorobis(triphenylphosphine)palladiumHCID 6102075—
SolventDichloromethaneHCID 6344—
Product1,4-Dichloro-2-ethynylbenzeneHCID 1263975489.3%

Reaction Steps

The title compound was prepared according to the procedure described in step-5 and step-6 of Intermediate-2 by using 1,4-dichloro-2-iodobenzene (1.0 g, 3.6 mmol), ethynyl(trimethyl)silane (0.541 g, 5.5 mmol), copper iodide (0.027 g, 0.14 mmol), bis(triphenylphosphine) palladium(II) chloride (0.050 g, 0.072 mmol), TBAF (catalytic) and DCM to afford 0.550 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 4.73 (s, 1H), 7.50 (d, J=8.7 Hz, 1H), 7.58 (d, J=8.7 Hz, 1H), 7.71 (s, 1H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09096545B2
Source datasetuspto-grants-2015_08
ORD IDord-7ce3ea261060435298aaac3573c4cbf9
Source noteuspto-grants-2015_08