1,3,5-Trichlorobenzene → 3,5-Dichlorophenyl methyl sulfide

HRID 479881Notes

Reaction equation

HRID 479881 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[CH:5]=[C:4]([Cl:9])[CH:3]=1.[CH3:10][S-:11].[Na+]>[Br-].C([P+](CCCC)(CCCC)CCCC)CCC>[CH3:10][S:11][C:6]1[CH:7]=[C:2]([Cl:1])[CH:3]=[C:4]([Cl:9])[CH:5]=1

Participants

4

Reactant 2

HCID 79501,3,5-TrichlorobenzeneHCID 4378561Sodium methanethiolate

Product 1

HCID 1292783,5-Dichlorophenyl methyl sulfide

Reagents, catalysts & solvents 1

HCID 76564Tetrabutylphosphonium bromideCatalyst

Procedure

A 4-necked, 1-liter flask equipped with a stirrer, a thermometer and a condenser tube was charged with 181.5 g (1.00 mole) of 1,3,5-trichlorobenzene and 67.9 g (0.10 mole) of an aqueous solution of 50 wt % tetra-n-butylphosphonium bromide. 233.6 g (1.00 mole) of an aqueous solution of 30 wt % sodium thiomethoxide was added dropwise at 80° C. over a period of 6 hours. After addition, the mixture was reacted at the same temperature for 10 hours. After completion of reaction, 191.9 g of a crude 1-methylthio-3,5-dichlorobenzene was obtained by separation procedure.

Workup

  1. customA 4-necked, 1-liter flask equipped with a stirrer
  2. additionAfter addition
  3. customthe mixture was reacted at the same temperature for 10 hours
  4. customAfter completion of reaction

Sources & evidence

ORD record
ord-8c9ca190fcfe46279a6e2efe0852a56f
Source dataset
uspto-grants-2003_11
Patent number
US06646165B2

Reaction notes

Loading…