Water → 1-(Chloromethyl)-3-methanesulfonylbenzene

HRID 641820Notes

Reaction equation

HRID 641820 reaction equation
CS([Cl:5])(=O)=O.[CH3:6][S:7]([C:10]1[CH:11]=[C:12]([CH2:16]O)[CH:13]=[CH:14][CH:15]=1)(=[O:9])=[O:8].C(N(CC)CC)C.O>ClCCl>[Cl:5][CH2:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([S:7]([CH3:6])(=[O:9])=[O:8])[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 23549738(3-Methanesulfonylphenyl)methanol

Product 1

HCID 220504111-(Chloromethyl)-3-methanesulfonylbenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

0.267 ml (3.45 mmol) methanesulphonyl-chloride is added to o a solution of 584 mg (3.14 mmol) (3-methanesulphonyl-phenyl)-methanol and 0.66 ml (4.71 mmol) triethylamine in 6 ml dichloromethane. This reaction mixture is stirred at room temperature for 1 h and at 50° C. for additional 3 h. The reaction mixture is then poured into water and extracted twice with dichloromethane. The combined organic layers are washed with water and brine, dried, filtered and concentrated in vacuo to afford the title compound, which is used in the next step without further purification.

Workup

  1. extractionextracted twice with dichloromethane
  2. washThe combined organic layers are washed with water and brine
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-903b7cd9a24445279100e5bac88670d2
Source dataset
uspto-grants-2010_04
Patent number
US07696216B2

Reaction notes

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