Reaktion #511533

Reaktionsgleichung

water

4-methyl-2-nitroanisole

N-bromosuccinimide

benzoyl peroxide

→

4-methoxy-3-nitro benzyl bromide

Ausbeute 70.0%

Lösungsmittel

carbon tetrachloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux for 18 h
2. 2
   SonstigeA solid precipitate formed
3. 3
   Sonstigewas separated by filtration
4. 4
   ExtraktionThe aqueous filtrate was extracted with carbon tetrachloride (3×50 mL)
5. 5
   EinengenThe extract was concentrated under reduced pressure
6. 6
   Sonstigeto yield a solid product
7. 7
   SonstigeThe solid products (the filtered precipitate and product of evaporating the
8. 8
   Extraktionextract)
9. 9
   Sonstigerecrystallized from ethyl acetate-hexane

Vorschrift

A solution of 4-methyl-2-nitroanisole (25 mmol), N-bromosuccinimide (25 mmol) and benzoyl peroxide (2.5 mmol) in carbon tetrachloride (100 mL) was heated at reflux for 18 h. The heated mixture was then poured into water. A solid precipitate formed and was separated by filtration. The aqueous filtrate was extracted with carbon tetrachloride (3×50 mL). The extract was concentrated under reduced pressure to yield a solid product. The solid products (the filtered precipitate and product of evaporating the extract) were combined and recrystallized from ethyl acetate-hexane to yield 4-methoxy-3-nitro benzyl bromide as a crystalline product in 70-75% yield. m.p. 110-112° C.

Quelle