Hydrogen Bromide → 2,6-Bis(trifluoromethyl)benzyl bromide

HRID 254476Notes

Reaction equation

HRID 254476 reaction equation
[BrH:1].S(=O)(=O)(O)O.[F:7][C:8]([F:22])([F:21])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[C:10]=1[CH2:19]O>O>[Br:1][CH2:19][C:10]1[C:9]([C:8]([F:22])([F:21])[F:7])=[CH:14][CH:13]=[CH:12][C:11]=1[C:15]([F:18])([F:17])[F:16]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 1118Sulfuric AcidHCID 153464312,6-Bis(trifluoromethyl)benzenemethanol

Product 1

HCID 118513632,6-Bis(trifluoromethyl)benzyl bromide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1 ml of a mixture of 48% aqueous HBr solution and conc. sulfuric acid (2:1 v/v) were added 0.81 g (3.3 mmol) (2,6-bis-trifluoromethyl-phenyl)-methanol and the solution heated to reflux for 6 h. Then the reaction mixture was cooled to rt, diluted with water and extracted with tert-butyl methyl ether. The combined extracts were washed with brine, dried over Na2SO4, filtered and evaporated. Kugelrohr distillation provided 2-bromomethyl-1,3-bis-trifluoromethyl-benzene as colourless oil of b.p. 135-140° C./22 mbar: MS (EI): 307.9 and 305.9 (M+.), 227.1 (((M-Br)+.), 100%).

Workup

  1. temperaturethe solution heated
  2. temperatureto reflux for 6 h
  3. extractionextracted with tert-butyl methyl ether
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. distillationKugelrohr distillation

Sources & evidence

ORD record
ord-857bd6fca37f40abb00df775daeefabd
Source dataset
uspto-grants-2011_01
Patent number
US07875645B2

Reaction notes

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