Water → 2,7-Difluoro-3-methyl-9H-fluorenone

HRID 1460366Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1460366
[CH3:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[C:14]([CH3:19])[CH:13]=2)=[C:4]([CH:8]=[C:9]([F:11])[CH:10]=1)C(O)=O.[OH2:20]>>[F:18][CH:15]1[C:14]([CH3:19])=[CH:13][C:12]2[C:3]3[C:2](=[CH:10][C:9]([F:11])=[CH:8][CH:4]=3)[CH2:1][C:17]=2[C:16]1=[O:20]

Komponenten

3

Edukt 2

HCID 962WaterHCID 19874639Methyl 2-(3-methyl-4-fluorophenyl)-5-fluorobenzoic acid

Produkt 1

HCID 679031352,7-Difluoro-3-methyl-9H-fluorenoneAusbeute 33 %

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

A stirred mixture of methyl 2-(3-methyl-4-fluorophenyl)-5-fluorobenzoic acid (6.5 g, 26.2 mmol) and polyphosphoric acid (30 g) was heated at 180° C. for 2 h. After the mixture had cooled to 80° C., it was poured into water (200 mL), and extracted with ethyl acetate. The combined extracts were washed with brine, dried over MgSO4, treated with charcoal, and concentrated. Chromatography on silica gel using 20% toluene in hexane provided 2 g (33%) of the desired ketone.

Aufarbeitung

  1. temperatureAfter the mixture had cooled to 80° C.
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. additiontreated with charcoal
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6f07452d71e54036be21ab2e942164f0
Quelldatensatz
uspto-grants-1991_12
Patentnummer
US05070100

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