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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2102916Generated: October 31, 2026

3,3-Dimethyl-1-butyne → HCID 57804220, compound

https://huagongshe.com/reaction/2102916

Reaction equation

Participants

RoleNameHCIDCharge
Reactant3,3-Dimethyl-1-butyneHCID 13512—
ReactantMethyl 4-bromo-2-methoxybenzoateHCID 15128242—
CatalystCopper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 24350—
CatalystHCID 178418476HCID 178418476—
SolventTriethylamineHCID 8471—
ProductHCID 57804220HCID 5780422091.1%

Reaction Conditions

Temperature100 °C

Reaction Steps

A mixture of methyl 4-bromo-2-methoxybenzoate (1.2 g, 0.0049 mol), copper(I) iodide (0.093 g, 0.00049 mol), 3,3-dimethyl-1-butyne (0.70 mL, 0.0059 mol) and bis(triphenylphosphine)palladium(II) chloride (0.34 g, 0.00049 mol) in Et3N (10 mL) was heated at 100° C. in a 50 mL sealed reaction vessel for 16 hours. After cooling, the mixture was filtered through Celite® and the filter cake was washed repeatedly with ethyl acetate. The filtrate was concentrated under vacuum and the residue was purified by column chromatography on silica gel to give a viscous oil (1.10 g, 91%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07576099B2
Source datasetuspto-grants-2009_08
ORD IDord-6873cdab8e4145bbaea831c60fe7619d
Source noteuspto-grants-2009_08