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

HRID 374844Notes

Reaction equation

HRID 374844 reaction equation
[F:1][C:2]([F:18])([F:17])[CH2:3][C:4]1([C:13]([F:16])([F:15])[F:14])[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5]1.[Br:19]Br>C(Cl)(Cl)(Cl)Cl.[Fe](Cl)(Cl)Cl>[Br:19][C:11]1[CH:10]=[CH:9][C:7]2[O:8][C:4]([CH2:3][C:2]([F:1])([F:17])[F:18])([C:13]([F:15])([F:14])[F:16])[O:5][C:6]=2[CH:12]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 536673032-(2,2,2-Trifluoroethyl)-2-(trifluoromethyl)-1,3-benzodioxole

Product 1

HCID 189959475-Bromo-2-(2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

54.4 g of 2-(2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole were dissolved in 300 ml of carbon tetrachloride, and 0.4 g of anhydrous iron(III) chloride was added. 32 g of bromine were then added dropwise at the reflux temperature and the mixture was subsequently stirred until the reaction was complete (monitoring by gas chromatography). The mixture was then allowed to cool, and was washed with 10% strength by weight aqueous sodium hydrogen sulphide solution and water, dried with magnesium sulphate and concentrated. The residue was distilled in vacuo. The yield was 58 g (83% of theory), and the boiling point was 80° C. under 14 mbar. The characteristic absorptions in the NMR spectra were as follows: 19F-NMR: -59.2 and -84.9 ppm. 1H-NMR: 3.02 ppm.

Workup

  1. temperatureto cool
  2. washwas washed with 10% strength by weight aqueous sodium hydrogen sulphide solution and water
  3. dry with materialdried with magnesium sulphate
  4. concentrationconcentrated
  5. distillationThe residue was distilled in vacuo

Sources & evidence

ORD record
ord-c067052e50c74692ae75355a06148809
Source dataset
uspto-grants-1996_01
Patent number
US05482956

Reaction notes

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