1,4-Dichlorobenzene → 1-Chloro-4-(methylthio)benzene

HRID 479882Notes

Reaction equation

HRID 479882 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](Cl)=[CH:4][CH:3]=1.[CH3:9][S-:10].[Na+]>[Br-].C([P+](CCCC)(CCCC)CCCC)CCC>[CH3:9][S:10][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 46851,4-DichlorobenzeneHCID 4378561Sodium methanethiolate

Product 1

HCID 312431-Chloro-4-(methylthio)benzene

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 147.0 g (1.00 mole) of 1,4-dichlorobenzene 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, 157.4 g of a crude 1-methylthio-4-chlorobenzene 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-41d7139bb4ee4a088c43102e27a9679a
Source dataset
uspto-grants-2003_11
Patent number
US06646165B2

Reaction notes

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