N-bromobutanimide → 2-Methoxyphenyl 2-methoxy-3-bromomethylphenyl ether

HRID 1163976Notes

Reaction equation

HRID 1163976 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:12]=1[O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH3:26]>C1C=CC=CC=1.N(C(C)(C)C#N)=NC(C)(C)C#N>[CH3:9][O:10][C:11]1[C:16]([CH2:17][Br:1])=[CH:15][CH:14]=[CH:13][C:12]=1[O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH3:26]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 130666562-Methoxyphenyl 2-methoxy-3-methylphenyl ether

Product 1

HCID 130666572-Methoxyphenyl 2-methoxy-3-bromomethylphenyl etherYield 101.6%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 241BenzeneSolvent

Procedure

N-Bromosuccinimide (6.56 g) and 2,2'-azobisisobutyronitrile (100 mg) were added to a solution of 2-methoxyphenyl 2-methoxy-3-methylphenyl ether (9.0 g) in benzene (100 ml), and the mixture was refluxed under heating for 2 hrs. The reaction mixture was evaporated, and water was added to the residue. The mixture was extracted with diethyl ether, and the extract was washed with water, dried over magnesium sulfate and then evaporated to give oily residue of 2-methoxyphenyl 2-methoxy-3-bromomethylphenyl ether (12.10 g).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 2 hrs
  3. customThe reaction mixture was evaporated
  4. additionwater was added to the residue
  5. extractionThe mixture was extracted with diethyl ether
  6. washthe extract was washed with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-04f85c56c26e4a01b2accc39660b98bd
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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