Bromine → 1-(Chloromethyl)-4-((trifluoromethyl)sulfanyl)benzene

HRID 894541Notes

Reaction equation

HRID 894541 reaction equation
[F:1][C:2]([S:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)([F:4])[F:3].BrBr.[Cl:15]Cl>C(Cl)(Cl)(Cl)Cl>[F:1][C:2]([S:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][Cl:15])=[CH:8][CH:7]=1)([F:4])[F:3]

Participants

5

Reactant 3

HCID 24408Bromine2×HCID 24526ChlorineHCID 27779084-(Trifluoromethylthio)toluene

Product 1

HCID 27831641-(Chloromethyl)-4-((trifluoromethyl)sulfanyl)benzeneYield 87.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

700 g of 4-trifluoromethylmercapto-toluene in 2,000 ml of CCl4 were initially introduced into a glass chlorination apparatus and heated to the reflux temperature. The solution was irradiated with a UV lamp. 3 ml of bromine were added before the start of the chlorination. When the color of the bromine had disappeared, 200 g of chlorine were passed in over a period of 6 hours. By fractional distillation over a 40 cm packed column, in addition to non-chlorinated starting material, 560 g of 4-trifluoromethylmercaptobenzyl chloride were obtained. Boiling point=97°-8° C./14 mm Hg, nD20 =1.5072.

Workup

  1. temperatureheated to the reflux temperature
  2. customThe solution was irradiated with a UV lamp
  3. customwere passed in over a period of 6 hours
  4. distillationBy fractional distillation over a 40 cm
  5. additionin addition

Sources & evidence

ORD record
ord-70fbfbfcafc540dbbd3833a23631efce
Source dataset
uspto-grants-1981_08
Patent number
US04284643

Reaction notes

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