Реакция #366014

Уравнение реакции

Hexylmagnesium bromide

3,3′-dibromo-2,2′-bithiophene

HCl

→

oil

Выход 100.1%

3,3′-Dihexyl-2,2′-bithiophene

Выход 100.1%

Растворители

diethyl ether

Условия реакции

Обработка

1. 1
   Температураheated for 24 h
2. 2
   Экстракцияextracted with ether
3. 3
   СушкаThe combined extracts were dried over anhydrous MgSO4
4. 4
   Фильтрацияfiltered
5. 5
   ДругоеAfter removal of the solvent
6. 6
   workup.DISTILLATIONthe residue was vacuum-distilled

Методика

Hexylmagnesium bromide (100 ml, 2 M solution in diethyl ether, 200 mol) was added dropwise to a solution of 3,3′-dibromo-2,2′-bithiophene (15 g, 46.6 mmol) and Ni(dppp)Cl2 (0.5 g, 0.1 mmol) in 100 ml of diethyl ether at 0° C. The reaction was slightly exothermic and a red brown coloration was observed. After stirred and heated for 24 h, the reaction mixture was cautiously poured into a mixture of crushed ice and diluted HCl solution and extracted with ether. The combined extracts were dried over anhydrous MgSO4 and filtered. After removal of the solvent, the residue was vacuum-distilled to give a clear viscous oil (15.6 g, 81%). 1H-NMR (CDCl3, ppm): δ7.25 (d, 2H, J=5 Hz), 6.96 (d, 2H, J=5 Hz), 2.50 (t, 4H), 1.54 (m, 4H), 1.23 (m, 12H), 0.85 (t, 6H).

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