Toluene → 5-(chlorosulfonyl)-2-methoxyphenyl Methanesulfonate

HRID 2140

Reaktionsgleichung

Reaktionsgleichung von HRID 2140
[CH3:1][S:2]([O:5]COC1C=CC=CC=1)(=[O:4])=[O:3].[Cl:14][S:15]([OH:18])(=O)=[O:16].C(Cl)(=O)[C:20](Cl)=[O:21].[C:25]1(C)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>ClCCl.CN(C=O)C>[CH3:1][S:2]([O:5][C:26]1[CH:27]=[C:28]([S:15]([Cl:14])(=[O:18])=[O:16])[CH:29]=[CH:30][C:25]=1[O:21][CH3:20])(=[O:4])=[O:3]

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 24638Chlorosulfonic acidHCID 65578Oxalyl chloride2×HCID 196896432-(Methanesulphonyloxy)methoxybenzene

Produkt 1

HCID 196896415-(chlorosulfonyl)-2-methoxyphenyl Methanesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

A solution of 2-(methanesulphonyloxy)methoxybenzene (0.822 g) in dichloromethane (15 ml) was stirred and cooled to -10° C. under a nitrogen atmosphere. A solution of chlorosulphonic acid (0.27 ml) in dichloromethane (5 ml) was then added dropwise over a period of 1 hour, maintaining the temperature below 0° C. The mixture was stirred for a further 4 hours, allowing the temperature to rise to 10° C. The mixture was evaporated to dryness in vacuo to yield an oil which was suspended in toluene (20 ml) with stirring under a nitrogen atmosphere. Oxalyl chloride (0.36 ml) was added dropwise, followed by the addition of DMF (5 drops). After stirring for 2 hours at room temperature, dichloromethane (15 ml) and oxalyl chloride (0.36 ml) were added and the reaction stirred overnight. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica, eluting with 60% ethyl acetate in hexane to furnish the title compound (0.99 g) as a white crystalline solid.

Aufarbeitung

  1. temperaturemaintaining the temperature below 0° C
  2. customto rise to 10° C
  3. customThe mixture was evaporated to dryness in vacuo
  4. customto yield an oil which
  5. stirringwith stirring under a nitrogen atmosphere
  6. stirringAfter stirring for 2 hours at room temperature
  7. stirringthe reaction stirred overnight
  8. customThe solvent was evaporated in vacuo
  9. customthe residue was purified by column chromatography on silica
  10. washeluting with 60% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-0c015ee7e7924c23b9f14267ea629a04
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05728712

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