Thionyl Chloride → 1-(Chloromethyl)-2-(methylsulfanyl)benzene

HRID 2303439Notes

Reaction equation

HRID 2303439 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][CH3:10].O=S(Cl)[Cl:13]>C(Cl)Cl>[Cl:13][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][CH3:10]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 3551404(2-Methylsulfanylphenyl)methanol

Product 1

HCID 124145821-(Chloromethyl)-2-(methylsulfanyl)benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Hydroxymethyl-1-methylthiobenzene (3.3 g, 21 mmol) is dissolved in 20 ml of absolute CH2Cl2 under an argon atmosphere. A solution of SOCl2 (2.6 g, 21 mmol) in 10 ml of absolute CH2Cl2 is added dropwise with stirring to this initial mixture in the course of 15 min, first under reflux, then at an internal temperature of 30° C. The reaction mixture is stirred under reflux for 2.25 h. The reaction mixture is concentrated and the oily crude product is purified by bulb tube distillation (7.9×10−2 mbar, 125-140° C.): colorless oil; yield: 3.3 g (88%).

Workup

  1. temperaturefirst under reflux
  2. customat an internal temperature of 30° C
  3. temperatureunder reflux for 2.25 h
  4. concentrationThe reaction mixture is concentrated
  5. customthe oily crude product is purified by bulb tube
  6. distillationdistillation (7.9×10−2 mbar, 125-140° C.)

Sources & evidence

ORD record
ord-ae0945fb2ca344caaf5993620ddfea24
Source dataset
uspto-grants-2002_08
Patent number
US06432988B1

Reaction notes

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