(Trifluoromethyl)benzene → Benzene, 1-bromo-3-(trifluoromethyl)-

HRID 2229893Notes

Reaction equation

HRID 2229893 reaction equation
[Br:1]Br.[C:3]1([C:9]([F:12])([F:11])[F:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[O-]S([O-])(=S)=O.[Na+].[Na+]>O>[Br:1][C:5]1[CH:4]=[C:3]([C:9]([F:12])([F:11])[F:10])[CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 7368(Trifluoromethyl)benzene2×HCID 24408BromineHCID 24477Sodium Thiosulfate

Product 1

HCID 9817Benzene, 1-bromo-3-(trifluoromethyl)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3280 g of bromine are added to a mixture of 6046 g benzotrifluoride, 68 g FeCl3 and 2 g SiO2 at about 20° C. within ca. 2 hours. The reaction temperature is then slowly rised within ca. 7 hours to ca 40° C., 300 g water and 130 g Na2S2O3 are added and stirred for ca. 15 minutes. The phases are separated and the organic phase is destilled resulting in 4160 g bromo-benzotrifluoride (isomeric ratio 3:4=96:4) and 3290 g benzotrifluoride which is recycled.

Workup

  1. additionare added
  2. customThe phases are separated
  3. customthe organic phase is destilled resulting in 4160 g bromo-benzotrifluoride (isomeric ratio 3:4=96:4)

Sources & evidence

ORD record
ord-5ab084e949b34ab399eabe53e1dba916
Source dataset
uspto-grants-2002_07
Patent number
US06420608B1

Reaction notes

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