Azobisisobutyronitrile → 4-(Difluoromethoxy)benzyl Bromide

HRID 1995673Notes

Reaction equation

HRID 1995673 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-9b6ebbc0c3ee42a69c80b52d37d69a4c
Source dataset
uspto-grants-1983_09
Patent number
US04405639

Reaction notes

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