Реакция #64641

Уравнение реакции

4-bromo-2-methyl-2-butene

Compound 45

4-bromo-2-methyl-2-butene

4-bromothiophenol

4-bromo-thiophenol

Compound 40

4-bromo-thiophenol

sodium hydroxide

→

title compound

4-Bromophenyl 3-methyl-2-butenyl sulfide

Растворители

acetone

acetone

Условия реакции

Обработка

1. 1
   Температураwas heated
2. 2
   Температураat reflux under argon for 2.5 hours
3. 3
   Температураthe mixture heated
4. 4
   Температураat reflux for a further 24 hours
5. 5
   ТемператураThe mixture was then cooled
6. 6
   Другоеsolvent removed in-vacuo
7. 7
   workup.ADDITIONThe residue was treated with 50 ml water
8. 8
   Экстракцияextracted with 3×75 ml ether
9. 9
   Промывкаwashed successively with 3×30 ml of 5% NaOH, 50 ml of water and 50 ml of saturated NaCl
10. 10
    Сушкаdried (MgSO4)
11. 11
    ДругоеSolvent was then removed in-vacuo
12. 12
    workup.DISTILLATIONthe residual oil purified by kugelrohr distillation (70 degrees C., 0.1 mm)

Методика

A mixture of 12.8 g (67.7 mmol) of 4-bromothiophenol (Compound 40) and 2.7 g (67.7 mmol) of sodium hydroxide in 50 ml acetone was heated at reflux under argon for 2.5 hours. The refluxing mixture was then treated dropwise with a solution of 10.0 g (67.1 mmol) of 4-bromo-2-methyl-2-butene (Compound 45) in 10 ml acetone and the mixture heated at reflux for a further 24 hours. The mixture was then cooled and solvent removed in-vacuo. The residue was treated with 50 ml water and extracted with 3×75 ml ether. The ether extracts were combined and washed successively with 3×30 ml of 5% NaOH, 50 ml of water and 50 ml of saturated NaCl and then dried (MgSO4). Solvent was then removed in-vacuo and the residual oil purified by kugelrohr distillation (70 degrees C., 0.1 mm) to give the title compound as a colourless oil. PMR (CDCl3 ): & 1.58 (3H, s), 1.70 (3H, s) 3.5 (2H, d, J~7.0 Hz), 5.27 (1H, t, J~7.0 Hz), 7.17 (2H, d, J~8.3 Hz), 7.36 (2H, d, J~8.3 Hz).

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