Azobisisobutyronitrile → 4-(Bromomethyl)-2,2-difluoro-1,3-dioxaindane

HRID 476976Notes

Reaction equation

HRID 476976 reaction equation
[F:1][C:2]1([F:12])[O:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([CH3:11])[C:4]=2[O:3]1.N(C(C)(C)C#N)=NC(C)(C)C#N.[Br:25]N1C(=O)CCC1=O>C(Cl)Cl>[Br:25][CH2:11][C:10]1[C:4]2[O:3][C:2]([F:1])([F:12])[O:6][C:5]=2[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 108775871,3-Benzodioxole, 2,2-difluoro-4-methyl-

Product 1

HCID 109994864-(Bromomethyl)-2,2-difluoro-1,3-dioxaindane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

76 g of 2,2-difluoro-4-methyl-1,3-benzodioxole and 200 mg of Azobisisobutyronitrile are added to a suspension of 90 g of N-bromosuccinimide in 400 ml of methylene chloride. The mixture is then heated under reflux, with stirring, until all the undissolved material floats to the top. After cooling, the succinimide is filtered off with suction and rinsed with carbon tetrachloride and the solution is then distilled in order to separate off the carbon tetrachloride. 117 g of crude benzyl bromide remain in the residue and are employed without purification.

Workup

  1. temperatureThe mixture is then heated
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. filtrationthe succinimide is filtered off with suction
  5. washrinsed with carbon tetrachloride
  6. distillationthe solution is then distilled in order
  7. customto separate off the carbon tetrachloride
  8. customare employed without purification

Sources & evidence

ORD record
ord-75599d6ab0d0407dba57eb512a4a4053
Source dataset
uspto-grants-1989_12
Patent number
US04886816

Reaction notes

Loading…