Sulfuric Acid → 2-(2-Fluorobenzyl)-3-thiophenecarboxaldehyde

HRID 256912Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 256912
S(=O)(=O)(O)O.C[O:7][CH:8](OC)[C:9]1[CH:13]=[CH:12][S:11][C:10]=1[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[F:21]>ClCCl>[F:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH2:14][C:10]1[S:11][CH:12]=[CH:13][C:9]=1[CH:8]=[O:7]

Komponenten

4

Edukt 2

HCID 1118Sulfuric AcidHCID 15728745HCID 15728745, Verbindung

Produkt 1

HCID 157287462-(2-Fluorobenzyl)-3-thiophenecarboxaldehydeAusbeute 23,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To silica gel (100 g), 15% aqueous sulfuric acid (15.4 g), and dichloromethane (400 ml) was added 2-(2-fluorobenzyl)-3-thiophenecarboxaldehyde dimethylacetal and dichloromethane (25 ml). The mixture was stirred for 2.5 hrs. The reaction mixture was filtered. The filter cake was washed with ethyl acetate and dichloromethane. The filtrate was concentrated and the residue was purified by flash column chromatography (silica gel, 0.5-10% ethyl acetate/hexanes) to afford 24.0 g (23.5%) of 2-(2-fluorobenzyl)-3-thiophenecarboxaldehyde.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. washThe filter cake was washed with ethyl acetate and dichloromethane
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by flash column chromatography (silica gel, 0.5-10% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-74c9cbe69f214dfba5e32cd6dc78da3e
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05260319

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