4-(2,3-Dihydroxypropyl)-2-fluorobenzonitrile → 2-Fluoro-4-(2-oxoethyl)benzonitrile

HRID 1519599Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1519599
[OH:1][CH:2](CO)[CH2:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([F:12])[CH:5]=1>CO.O>[F:12][C:6]1[CH:5]=[C:4]([CH2:3][CH:2]=[O:1])[CH:11]=[CH:10][C:7]=1[C:8]#[N:9]

Komponenten

4

Edukt 1

HCID 675132414-(2,3-Dihydroxypropyl)-2-fluorobenzonitrile

Produkt 1

HCID 866944782-Fluoro-4-(2-oxoethyl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 4-(2,3-dihydroxypropyl)-2-fluorobenzonitrile (500 mg, 2.6 mmol) in 10 mL of methanol and 3 mL of water was cooled to 0° C. by ice bath, then NaIO4 (820 mg, 3.8 mmol) was added and the mixture was stirred at 0° C. for two hours. The reaction was monitored according to TLC. The mixture was filtered and concentrated. The residue was dissolved in DCM, dried over anhydrous sodium sulfate, and then purified by flash column chromatography to give 2-fluoro-4-(2-oxoethyl)benzonitrile. MS m/z: 164 (M+1)+.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in DCM
  4. dry with materialdried over anhydrous sodium sulfate
  5. custompurified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e6da56c1e0494bd09f771de800ef92c3
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073882B2

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