Trimethylsilylacetylene → [3-(2-Methoxy-1,1-dimethyl-ethyl)-phenylethynyl]-trimethyl-silane

Participants

Role	Name	HCID	Charge
Reactant	Trimethylsilylacetylene	HCID 66111	—
Reactant	2-(3-Bromophenyl)-2-methylpropyl methyl ether	HCID 67191411	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	Acetonitrile triethylamine	HCID 21895542	—
Product	[3-(2-Methoxy-1,1-dimethyl-ethyl)-phenylethynyl]-trimethyl-silane	HCID 67187907	89%

Reaction Steps

To a solution of 1-bromo-3-(2-methoxy-1,1-dimethyl-ethyl)-benzene (1.62 g, 6.69 mmol) and trimethylsilylacetylene (1.2 mL, 8.7 mmol, 1.3 eq.) in MeCN-Et3N (50 mL, 7:3) was added Pd(PPh3)2Cl2 (0.23 g, 0.33 mmol. 0.05 eq.), CuI (0.038 g, 0.2 mmol, 0.03 eq.) and the mixture refluxed for 16 h. After cooling to ambient temperature and concentration under reduced pressure the residue was chromatographed (EtOAc-hexane, 2:98) to obtain 1.54 g (89%) of the desired product. NMR (DMSO-d6): 7.28-7.00 (m, 4H), 3.16 (s, 2H), 2.98 (s, 3H), 1.00 (s, 6H), 0.1 (s, 9H). MS (DCI): 261 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08071762B2
Source dataset	uspto-grants-2011_12
ORD ID	ord-eee81f1a332f4e57bc3191f2418cb4b6
Source note	uspto-grants-2011_12