Реакция #78290

Уравнение реакции

phenol

2-chloro-5-nitrophenol

potassium carbonate

4-bromo-2-methyl-2-butene

prenyl bromide

→

1-chloro-2-(3-methyl-2-butenyloxy)-4-nitrobenzene

Растворители

methyl ethyl ketone

Условия реакции

Обработка

1. 1
   workup.STIRRINGstirred for 2 hours
2. 2
   ДругоеThe solvent was then removed from the reaction mixture
3. 3
   workup.ADDITIONThe residue of the reaction mixture was then treated with water
4. 4
   Экстракцияextracted into diethyl ether
5. 5
   ПромывкаThe extract was washed with 2N sodium hydroxide and water
6. 6
   Сушкаdried (MgSO4)
7. 7
   Фильтрацияfiltered
8. 8
   Другоеevaporated
9. 9
   Другоеto leave a brown solid which
10. 10
    Другоеwas recrystallised from ethyl acetate/isopropyl alcohol

Методика

A reaction mixture of 2-chloro-5-nitrophenol (50.6 g), anhydrous potassium carbonate (44.5 g), tetrabutylammonium bromide (4.7 g) and 4-bromo-2-methyl-2-butene (53.3 g, 90%) in methyl ethyl ketone (263 mL) was stirred at ambient temperature overnight. TLC of the reaction mixture showed traces of phenol remaining. Additional prenyl bromide (1 mL) was then added to the reaction mixture and stirred for 2 hours. The solvent was then removed from the reaction mixture. The residue of the reaction mixture was then treated with water and extracted into diethyl ether. The extract was washed with 2N sodium hydroxide and water, dried (MgSO4), filtered, and evaporated, to leave a brown solid which was recrystallised from ethyl acetate/isopropyl alcohol to give 1-chloro-2-(3-methyl-2-butenyloxy)-4-nitrobenzene, 49.5 g, a beige solid, a single spot on TLC (ethyl acetate:hexane, 20:80).

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