Water → 1-Chloro-2-methyl-3-(methylsulfanyl)benzene

HRID 322051

Reaction equation

HRID 322051 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](Cl)[C:3]=1[CH3:9].[CH3:10][S-:11].[Na+].IC.O>CN(C)P(N(C)C)(N(C)C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:11][CH3:10])[C:3]=1[CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 83682,6-DichlorotolueneHCID 4378561Sodium methanethiolate

Product 1

HCID 148011761-Chloro-2-methyl-3-(methylsulfanyl)benzene

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
100 °C

Procedure

200 g (1.24 mol) of 2,6-dichlorotoluene were dissolved in 600 ml of hexamethylphosphoramide and treated with 130.41 g (1.86 mol) of sodium thiomethoxide. The mixture was then heated at 100° C. for 3 h. It was allowed to cool, 88.2 g (0.5 mol) of iodomethane were added and it was stirred at room temperature for 0.5 h. The mixture was then added to 3.5 l of water and extracted with ethyl acetate. The combined organic phases were washed with water, dried over MgSO4 and completely concentrated on a rotary evaporator.

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phases were washed with water
  4. dry with materialdried over MgSO4
  5. concentrationcompletely concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-ca30d054c6794f18968eebe666d91b7b
Source dataset
uspto-grants-2001_04
Patent number
US06211216B1

Linked notes

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