Phosphorus pentachloride → 2-(4-Fluoro-phenyl)-ethanesulfonyl chloride

HRID 433891Notes

Reaction equation

HRID 433891 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[Na+].[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][S:17]([O-:20])(=O)=[O:18])=[CH:11][CH:10]=1>C1(C)C=CC=CC=1.O>[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][S:17]([Cl:2])(=[O:20])=[O:18])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 88013906HCID 88013906, compound

Product 1

HCID 27590982-(4-Fluoro-phenyl)-ethanesulfonyl chlorideYield 34.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Phosphorus pentachloride (5.6 g, 27 mmol) was added portionwise over 10 minutes to a stirred suspension of 2-(4-fluorophenyl)ethanesulfonic acid sodium salt (9 mmol, contaminated with sodium bromide, total weight 2.87 g) in dry toluene (15 ml) at room temperature. The reaction mixture was heated under reflux for 90 minutes and was then stirred at room temperature overnight. The reaction mixture was diluted with water (20 ml) and the organic phase was separated. The aqueous phase was extracted with dichloromethane (20 ml) and the organic extracts were combined, dried over magnesium sulfate and concentrated under vacuum to give the title compound as an oil, (0.7 g) Rf 0.92 (dichloromethane).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 90 minutes
  3. customthe organic phase was separated
  4. extractionThe aqueous phase was extracted with dichloromethane (20 ml)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2a08a71599cb4af29a3e0b28cc524929
Source dataset
uspto-grants-2003_12
Patent number
US06670362B2

Reaction notes

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