Bromine → 4-(Trifluoromethylthio)benzyl bromide

HRID 2050089Notes

Reaction equation

HRID 2050089 reaction equation
[Br:1]Br.[F:3][C:4]([F:14])([F:13])[S:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:12][C:9]1[CH:8]=[CH:7][C:6]([S:5][C:4]([F:13])([F:3])[F:14])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 27779084-(Trifluoromethylthio)toluene

Product 1

HCID 27778824-(Trifluoromethylthio)benzyl bromide

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

Bromine (20.5 g, 0.13 mol) in 20 ml of carbon tetrachloride is added slowly to a solution of 4-trifluoromethylthiotoluene (29 g, 0.15 mol) in 90 ml of carbon tetrachloride heated to gentle reflux under a 275 W sunlamp. When the addition is complete, the solution is maintained at reflux for one hour. Most of the solvent is removed at atmospheric pressure, then the residue is vacuum distilled. The 15.5 g cut with boiling point 64°-77° C./0.6-0.8 mm is 92% monobromo compound by glc.

Workup

  1. temperatureheated
  2. temperatureto gentle reflux under a 275 W sunlamp
  3. additionWhen the addition
  4. temperaturethe solution is maintained
  5. temperatureat reflux for one hour
  6. customMost of the solvent is removed at atmospheric pressure
  7. distillationdistilled

Sources & evidence

ORD record
ord-b1581565b0914fc785a2eb9fe600e60a
Source dataset
uspto-grants-1980_04
Patent number
US04199595

Reaction notes

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