Phosphorus pentachloride → 4-[(4-Fluorophenyl)methoxy]benzene-1-sulfonyl chloride

HRID 1531233Notes

Reaction equation

HRID 1531233 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([S:14]([O-])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Na+].P(Cl)(Cl)(Cl)(Cl)[Cl:22]>C(Cl)Cl>[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([S:14]([Cl:22])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 23701365Sodium 4-(4-fluorobenzyloxy)benzenesulfonate

Product 1

HCID 181794244-[(4-Fluorophenyl)methoxy]benzene-1-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a slurry of sodium 4-(4-fluorobenzyloxy)benzenesulfonate (0.5 grams, 1.64 mmole), in methylene chloride (5 mL) was added phosphorus pentachloride (275 mg, 1.31 mmole). The resulting mixture was heated at reflux for 7 hours. After cooling in an ice bath and quenching with water (15 mL), the mixture was extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate, and concentrated to afford 4-(4-fluorobenzyloxy)benzenesulfonyl chloride a white solid (130 mg, 26%).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 7 hours
  3. temperatureAfter cooling in an ice bath
  4. customquenching with water (15 mL)
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic phase was washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-785337ec893c4b19a24baf89bfaa7986
Source dataset
uspto-grants-2001_03
Patent number
US06197810B1

Reaction notes

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