反应详情

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.

1. temperatureat reflux for 18 h
2. customA solid precipitate formed
3. customwas separated by filtration
4. extractionThe aqueous filtrate was extracted with carbon tetrachloride (3×50 mL)
5. concentrationThe extract was concentrated under reduced pressure
6. customto yield a solid product
7. customThe solid products (the filtered precipitate and product of evaporating the
8. extractionextract)
9. customrecrystallized from ethyl acetate-hexane