Water → Benzene, 2-(bromomethyl)-1-methoxy-3-nitro-

HRID 37867

Reaction equation

HRID 37867 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[C:12]=1[CH3:20].O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][CH2:20][C:12]1[C:13]([N+:17]([O-:19])=[O:18])=[CH:14][CH:15]=[CH:16][C:11]=1[O:10][CH3:9]

Participants

6

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 785542-Methyl-3-nitroanisole

Product 1

HCID 186047Benzene, 2-(bromomethyl)-1-methoxy-3-nitro-Yield 86.7%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

N-bromosuccinimide (590 mg, 3.30 mmol) was added to a solution of 1-methoxy-2-methyl-3-nitro-benzene (500 mg, 3.0 mmol) in carbon tetrachloride (5 mL) followed by a catalytic amount of dibenzoyl peroxide (25 mg). The reaction mixture was heated at reflux for 3 h then cooled to room temperature and poured into water. The organic phase was separated, washed with water (2×20 mL), dried over the anhydrous sodium sulfate and concentrated in vacuo to afford 2-bromomethyl-1-methoxy-3-nitro-benzene (640 mg, 86%) as a solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 h
  3. customThe organic phase was separated
  4. washwashed with water (2×20 mL)
  5. dry with materialdried over the anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-61bbfe6c54e247c7b60bf5269a8079ba
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Linked notes

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