Bromine → 5-Bromo-2-(1-chloro-2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxol

HRID 374845Notes

Reaction equation

HRID 374845 reaction equation
[Cl:1][CH:2]([C:7]1([C:16]([F:19])([F:18])[F:17])[O:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[O:8]1)[C:3]([F:6])([F:5])[F:4].[Br:20]Br>C(Cl)(Cl)(Cl)Cl>[Br:20][C:13]1[CH:14]=[CH:15][C:9]2[O:8][C:7]([CH:2]([Cl:1])[C:3]([F:6])([F:5])[F:4])([C:16]([F:19])([F:18])[F:17])[O:11][C:10]=2[CH:12]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 544550482-(1-Chloro-2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole

Product 1

HCID 189959465-Bromo-2-(1-chloro-2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxol

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

51 g of 2-(1-chloro-2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole from Example 2 or 17 were dissolved in 300 ml of carbon tetrachloride, and 0.5 g of anhydrous FeCl3 was added. 32 g of bromine were then added and the mixture was stirred under reflux for 3 hours. After cooling, the mixture was washed with 10% strength NaHSO3 solution, dried with MgSO4 and distilled. The yield was 49 g (63% of theory), and the boiling point was 94°-98° C. under 8 mbar.

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureAfter cooling
  3. washthe mixture was washed with 10% strength NaHSO3 solution
  4. dry with materialdried with MgSO4
  5. distillationdistilled

Sources & evidence

ORD record
ord-1df99ce5ca30437f8e7ccc0c4b3af8fd
Source dataset
uspto-grants-1996_01
Patent number
US05482956

Reaction notes

Loading…