2-Chloroanisole → 3-Chloro-4-methoxybenzene-1-sulfonyl chloride

HRID 1044694Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1044694
[Cl:1][S:2]([OH:5])(=O)=[O:3].[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14]>>[Cl:6][C:7]1[CH:12]=[C:11]([S:2]([Cl:1])(=[O:5])=[O:3])[CH:10]=[CH:9][C:8]=1[O:13][CH3:14]

Komponenten

3

Edukt 2

HCID 130112-ChloroanisoleHCID 24638Chlorosulfonic acid

Produkt 1

HCID 167674273-Chloro-4-methoxybenzene-1-sulfonyl chlorideAusbeute 50 %

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

Under N2 atmosphere, 41.25 mL chlorosulfonic acid was cooled in an ice bath, and under stirring 22.26 mL 2-chloroanisole was added dropwise. The mixture was heated to 55° C.; after 10 min. the heat source was removed and the mixture was stirred overnight at room temperature. The mixture was poured into ice water and extracted twice with DCM. The combined organic layers were dried over MgSO4 and evaporated to dryness. The residue was purified by flash chromatography (PA/EA 9:1) to give 24.94 g (50%) of a beige oil. 1H NMR (400 MHz, CDCl3) δ 4.03 (s, 3H), 7.08 (d, J=8.73 Hz, 1H), 7.94 (dd, J=9.03, 2.41 Hz, 1H), 8.06 (d, J=2.41 Hz, 1H).

Aufarbeitung

  1. additionwas added dropwise
  2. customafter 10 min. the heat source was removed
  3. additionThe mixture was poured into ice water
  4. extractionextracted twice with DCM
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. customevaporated to dryness
  7. customThe residue was purified by flash chromatography (PA/EA 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-d768417ac70f43418a96319d0f0efe29
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563723B2

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