ChemicalBook CAS DataBase List 2-(TRIBUTYLSTANNYL)THIOPHENE

2-(TRIBUTYLSTANNYL)THIOPHENE synthesis

8synthesis methods

Product Name:2-(TRIBUTYLSTANNYL)THIOPHENE
CAS Number:54663-78-4
Molecular formula:C16H30SSn
Molecular Weight:373.18

1003-09-4 Synthesis

1003-09-4
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$10.00/25g

1461-22-9
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54663-78-4
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$25.00/5g

Yield:54663-78-4 90%

Reaction Conditions:

Stage #1:2-bromothiophene with n-butyllithium in tetrahydrofuran;hexane at -20; for 1 h;Inert atmosphere;
Stage #2:tributyltin chloride in tetrahydrofuran;hexane at -20 - 20;Inert atmosphere;

Steps:

1.1 (1) Synthesis of Intermediate 1
In three-necked 250mL flask were added 2-bromothiophene (4.89g, 30mmol) and 60mL of anhydrous tetrahydrofuran, and put on a constant pressure funnel, evacuated, purged with argon, the reaction flask was placed in cryostat reactor cooled to -20 deg. C, then added dropwise n-butyllithium (15mL, 33mmol) in n-hexane (2.2mol / L), the reaction was continued at -20 deg. C for 1h, then slowly added dropwise (8.95mL, 33mmol) tributyltin chloride, after the reaction 1h, the reaction flask was moved at room temperature overnight. The reaction was stopped, the reaction flask was added 150mL of deionized water, and extracted three times with dichloromethane (80mL × 3), then the organic layer was washed three times with saturated brine (100mL × 3), combined organic phase was dried over anhydrous magnesium sulfate overnight . The filtrate was collected by filtration, solvent was removed by rotary evaporation, and the residue was mixed with a small amount of triethylamine in petroleum ether as eluent to silica gel column chromatography, to give a colorless liquid 11.08g, 90% yield.

References:

Dongguan University of Technology;Liao, Junxu;Zhao, Hongbin;Han, Lifen;Peng, Zaixi;Zhang, Wentao;Liu, Chuansheng;Peng, Fei;Zong, Qiao CN105732680, 2016, A Location in patent:Paragraph 0021

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188290-36-0 Synthesis