Triethylamine → 2-Fluoro-4-methoxybenzaldehyde

HRID 636750Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 636750
C(N(CC)CC)C.[F:8][C:9]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:10]=1[CH2:11][OH:12].S(=O)(=O)=O.N1C=CC=CC=1.OS([O-])(=O)=O.[K+]>CS(C)=O>[F:8][C:9]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:10]=1[CH:11]=[O:12]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 168533Sulfur trioxide-pyridineHCID 516920Potassium bisulfateHCID 593638(2-Fluoro-4-methoxyphenyl)methanol

Produkt 1

HCID 27348732-Fluoro-4-methoxybenzaldehydeAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

Triethylamine (0.92 ml, 6.60 mmol) was added to a solution of 2-fluoro-4-methoxybenzylalcohol (346.9 mg, 2.22 mmol) in DMSO (8 ml). Pyridine sulfur trioxide (1.0501 g, 6.60 mmol) was added portionwise to the mixture checking raise of the temperature. The mixture was stirred for 0.5 hours. The mixture was added to 5% KHSO4 aqueous solution, extracted three times with ethyl acetate and dried over MgSO4. The mixture was concentrated and purified by silica gel chromatography (hexane/ether=5/1) to give the title compound (301 mg; 88%).

Aufarbeitung

  1. temperaturechecking raise of the temperature
  2. extractionextracted three times with ethyl acetate
  3. dry with materialdried over MgSO4
  4. concentrationThe mixture was concentrated
  5. custompurified by silica gel chromatography (hexane/ether=5/1)

Quellen und Nachweise

ORD-Eintrag
ord-ac5299c8024c4b5bbdb99c73ea3bd2e3
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06194461B1

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