Bromine → 4-(Trifluoromethylthio)benzyl bromide

HRID 1447922Notes

Reaction equation

HRID 1447922 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-33848459d5fe4598be95e840e4ccf4d5
Source dataset
uspto-grants-1979_12
Patent number
US04178460

Reaction notes

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