Thionyl Chloride → 1-(Chloromethyl)-4-(ethylsulfonyl)benzene

HRID 271475

Reaction equation

HRID 271475 reaction equation
[CH2:1]([S:3]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12]O)=[CH:8][CH:7]=1)(=[O:5])=[O:4])[CH3:2].S(Cl)([Cl:16])=O>ClCCl>[Cl:16][CH2:12][C:9]1[CH:10]=[CH:11][C:6]([S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 572424(4-(Ethylsulfonyl)phenyl)methanol

Product 1

HCID 598347911-(Chloromethyl)-4-(ethylsulfonyl)benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (4-(ethylsulfonyl)phenyl)methanol (200 mg, 1 mmol) and thionyl chloride (3 mL) was stirred at reflux for 4 h. The solvent was removed under reduced pressure to obtain a gum. Dichloromethane (10 mL) was added, and the mixture was stirred for 5 min and then concentrated under vacuum. This process was repeated two more times to ensure complete removal of thionyl chloride. After residual solvent removal under vacuum, 205 mg of the title compound was obtained as a white solid. HPLC/MS: retention time=2.308 min, [M+H]+=219.

Workup

  1. temperatureat reflux for 4 h
  2. customThe solvent was removed under reduced pressure
  3. customto obtain a gum
  4. stirringthe mixture was stirred for 5 min
  5. concentrationconcentrated under vacuum
  6. customremoval of thionyl chloride
  7. customAfter residual solvent removal under vacuum

Sources & evidence

ORD record
ord-da6685ace886414ead9b8f1d80fdfa93
Source dataset
uspto-grants-2008_11
Patent number
US07452892B2

Linked notes

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