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

HRID 2188725Notes

Reaction equation

HRID 2188725 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>[N+:10]([C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=1[O:8][CH3:9])[CH2:1][Br:13])([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 reaction mixture was then poured into water and solid separated was filtered. The aqueous layer was extracted with carbon tetrachloride (3×50 mL) and organic phase was separated and evaporated to give a solid product. The solid products were combined and recrystallized from ethyl acetate-hexane to give a crystalline product of 3-nitro-4-methoxy benzyl bromide. m.p. 110-112° C., yield 70-75%.

Workup

  1. temperatureat reflux for 18 h
  2. customseparated
  3. filtrationwas filtered
  4. extractionThe aqueous layer was extracted with carbon tetrachloride (3×50 mL) and organic phase
  5. customwas separated
  6. customevaporated
  7. customto give a solid product
  8. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-ed104d7c23844c50ad20ae64472dffe9
Source dataset
uspto-grants-2012_12
Patent number
US08324190B2

Reaction notes

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