Реакция #83907

Уравнение реакции

ethyl acetate

1,4-dibromobutane

4-bromo-1-(1,3-dithian-2-yl)ethylbenzene

sec-butyllithium

→

4-(4-bromobutyl)-1-(1,3-dithian-2-yl)ethylbenzene

Растворители

tetrahydrofuran

Условия реакции

Обработка

1. 1
   workup.STIRRINGAfter being stirred for 3 hours
2. 2
   Промывкаwashed with water and brine
3. 3
   СушкаThe organic solution was then dried (Na2SO4)
4. 4
   Концентрированиеconcentrated to an oil
5. 5
   ДругоеThe crude product was purified by flash chromatography over a silica gel column
6. 6
   ДругоеThe 4-(4-bromobutyl)-1-(1,3-dithian-2-yl)-ethylbenzene thus purified

Методика

A solution of 4-bromo-1-(1,3-dithian-2-yl)ethylbenzene (27.2 g, 94 mmol) in tetrahydrofuran (200 ml) was charged with sec-butyllithium (99 ml, 1.3M in cyclohexane, 0.13 mole) dropwise at -78° C. under nitrogen. The mixture was stirred at ambient temperature for 1.5 hours, and then quenched with 1,4-dibromobutane (42 g, 0.2 mole). After being stirred for 3 hours, the mixture was poured into ethyl acetate, and then washed with water and brine. The organic solution was then dried (Na2SO4) and concentrated to an oil. The crude product was purified by flash chromatography over a silica gel column. The 4-(4-bromobutyl)-1-(1,3-dithian-2-yl)-ethylbenzene thus purified was a light oil, 22.3 g.

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