Methanesulfonyl chloride → HCID 86605221, compound

HRID 1725344Notes

Reaction equation

HRID 1725344 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([F:12])[CH:11]=1)[O:5][CH2:6][CH2:7][OH:8].[CH3:13][S:14](Cl)(=[O:16])=[O:15]>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([F:12])[CH:11]=1)[O:5][CH2:6][CH2:7][O:8][S:14]([CH3:13])(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 22036323HCID 22036323, compound

Product 1

HCID 86605221HCID 86605221, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-(3,5-difluoro-phenoxy)-ethanol (2.5 g, 14.3 mmol) in pyridine (10 ml) was cooled with an ice bath and treated dropwise with methanesulfonyl chloride (1.7 g, 14.7 mmol). The ice bath was removed and the mixture was stirred for 16 hours at room temperature. The pyridine was evaporated in vacuo and the residue was dissolved in ethyl acetate. The organic phase was washed with water, with 2N hydrochloric acid then three times with water, dried over magnesium sulfate and concentrated. The residue was crystallised in diisopropyl ether to give methanesulfonic acid 2-(3,5-difluoro-phenoxy)-ethyl ester (1.8 g, 51%).

Workup

  1. customThe ice bath was removed
  2. customThe pyridine was evaporated in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe organic phase was washed with water, with 2N hydrochloric acid
  5. dry with materialthree times with water, dried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was crystallised in diisopropyl ether

Sources & evidence

ORD record
ord-697f9ca91d7543d088ef17e3d0826572
Source dataset
uspto-grants-2009_02
Patent number
US07491714B2

Reaction notes

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