tert-Butyl hydroperoxide → Benzene, 2-(bromomethyl)-1-methoxy-3-nitro-

HRID 1634720Notes

Reaction equation

HRID 1634720 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[C:4]=1[CH3:12].[Br:13]N1C(=O)CCC1=O.C(OO)(C)(C)C>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[C:4]=1[CH2:12][Br:13]

Participants

5

Reactant 3

HCID 6410tert-Butyl hydroperoxideHCID 67184N-bromobutanimideHCID 785542-Methyl-3-nitroanisole

Product 1

HCID 186047Benzene, 2-(bromomethyl)-1-methoxy-3-nitro-Yield 10.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 2-methoxy-6-nitrotoluene (28.2 g, 159 mmol) and N-bromosuccinimide (26.5 g, 159 mmol) in 350 mL CCl4 was treated with a catalytic amount of t-butylhydroperoxide and irradiated with a floodlamp while stirring for 3 hours. The solids formed were filtered and the filtrate concentrated to give 4.0 g of a yellow solid.

Workup

  1. customirradiated with a floodlamp
  2. customThe solids formed
  3. filtrationwere filtered
  4. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-143f1584979841c98927bbcb02fdb0d3
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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