Water → 4-(Bromomethyl)-1-methoxy-2-nitrobenzene

HRID 424351

Reaction equation

HRID 424351 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.O>C(Cl)(Cl)(Cl)Cl>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH2:1][Br:13])=[CH:3][C:4]=1[N+:10]([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 7187Benzoyl PeroxideHCID 670581-Methoxy-4-methyl-2-nitrobenzeneHCID 67184N-bromobutanimide

Product 1

HCID 115796484-(Bromomethyl)-1-methoxy-2-nitrobenzeneYield 70%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2366d8e276074115ab25da0842cd367e
Source dataset
uspto-grants-2012_01
Patent number
US08106033B2

Linked notes

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