Azobisisobutyronitrile → 4-(Difluoromethoxy)benzyl Bromide

HRID 1702546Notes

Reaction equation

HRID 1702546 reaction equation
[F:1][CH:2]([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1.[Br:12]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[F:1][CH:2]([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][Br:12])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 74104alpha,alpha-Difluoro-p-methylanisole

Product 1

HCID 27370014-(Difluoromethoxy)benzyl BromideYield 62.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

270 g of 4-difluoromethoxytoluene in 800 ml of CCl4 were initially introduced and 300 g N-bromo-succinimide were added. After adding a pinch of azobisisobutyronitrile, the mixture was heated to the reflux temperature. After 8 hours, it was cooled, the insoluble succinimide was filtered off and the residue on the filter was washed with CCl4. The carbon tetrachloride was distilled off from the reaction solution and the crude product was purified by fractional distillation. 250 g of 4-difluoromethoxy-benzyl bromide were obtained. Boiling point=82°-5° C./0.4 mm Hg; nD20 =1.5200.

Workup

  1. temperaturethe mixture was heated to the reflux temperature
  2. temperatureit was cooled
  3. filtrationthe insoluble succinimide was filtered off
  4. washthe residue on the filter was washed with CCl4
  5. distillationThe carbon tetrachloride was distilled off from the reaction solution
  6. distillationthe crude product was purified by fractional distillation

Sources & evidence

ORD record
ord-1c6a5c1f0a8f4cb9b1ac4fae98556a0e
Source dataset
uspto-grants-1982_09
Patent number
US04348323

Reaction notes

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