3,5-Dichloro-1-fluoropyridinium triflate → Methyl 5-fluoro-4-hydroxy-2-methoxybenzoate

HRID 1673

Reaktionsgleichung

Reaktionsgleichung von HRID 1673
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.[O-]S(C(F)(F)[F:19])(=O)=O.ClC1C=[N+](F)C=C(Cl)C=1>C(Cl)Cl>[F:19][C:11]1[C:2]([OH:1])=[CH:3][C:4]([O:12][CH3:13])=[C:5]([CH:10]=1)[C:6]([O:8][CH3:9])=[O:7]

Komponenten

4

Edukt 2

HCID 27245783,5-Dichloro-1-fluoropyridinium triflateHCID 12532676Methyl 4-hydroxy-2-methoxybenzoate

Produkt 1

HCID 18914108Methyl 5-fluoro-4-hydroxy-2-methoxybenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of the methyl 4-hydroxy-2-methoxybenzoate (1 g, 5 mmol, from Step 3) in CH2Cl2 (20 mL) was added 3,5-dichloro-1-fluoropyridinium triflate (2.25 g, 6 mmol). The solution was refluxed for 48 h and then cooled to ambient temperature and stripped down under reduced pressure. The crude oil was purified by pressurized silica gel column chromatography using 99:1 CH2Cl2 :MeOH. Evaporation of the CH2Cl2 :MeOH mixture gave the desired methyl 5-fluoro-4-hydroxy-2-methoxybenzoate as a white powder.

Aufarbeitung

  1. temperatureThe solution was refluxed for 48 h
  2. customThe crude oil was purified by pressurized silica gel column chromatography
  3. customEvaporation of the CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-48df0370b6c1448ea65c1fd6355a24c2
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726172

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