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ChemicalBook CAS DataBase List (4-METHOXYPHENYLETHYNYL)TRIMETHYLSILANE&
3989-14-8

(4-METHOXYPHENYLETHYNYL)TRIMETHYLSILANE& synthesis

13synthesis methods
-

Yield: 81%

Reaction Conditions:

with tetrakis(triphenylphosphine) palladium(0);sodium acetate at 80; for 5 h;Inert atmosphere;Green chemistry;Stille Cross Coupling;

Steps:

Stille cross-coupling reaction of organotin reagents with aryl bromides in PEG-400; general procedure
General procedure: A mixture of aryl bromide 1 (0.5 mmol), organotin reagent 2(0.6 mmol), NaOAc (0.5 mmol) and Pd(PPh3)4 (0.005 mmol) inPEG-400 (2 mL) was stirred at 80 °C under an argon atmosphere for3-5 h until complete consumption of the aryl bromide was observed as judged by TLC. After being cooled to room temperature, the mixture was extracted three times with light petroleum ether (30-60°C) (3 × 10 mL). The combined organic phases were concentrated under reduced pressure and the residue was purified by flash column chromatography on silica gel [light petroleum ether (30-60 °C)/ethylacetate] to afford the desired product 3.

References:

Huang, Xue;Yao, Fang;Wei, Ting;Cai, Mingzhong [Journal of Chemical Research,2017,vol. 41,# 9,p. 547 - 550]

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