Chlorotrimethylsilane → Methyl 2-Fluoro-5-nitrobenzoate

HRID 39045

Reaktionsgleichung

Reaktionsgleichung von HRID 39045
[F:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl[Si](C)(C)[CH3:16].CCCCCCC>CO>[CH3:16][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:2]=1[F:1]

Komponenten

5

Edukt 3

HCID 6397ChlorotrimethylsilaneHCID 8900HeptaneHCID 2809972-Fluoro-5-nitrobenzoic acid

Produkt 1

HCID 11217860Methyl 2-Fluoro-5-nitrobenzoateAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 2-fluoro-5-nitrobenzoic acid 10-1 (5.22 g, 28.2 mmol) in methanol (30 mL) was added chlorotrimethylsilane 10-2 (6.00 g, 1.96 eq.). The reaction mixture was stirred under reflux during 16 h, then cooled down to room temperature, concentrated and the resulting precipitate was filtered off, washed with a small quantity of methanol, then heptane, to provide 4.36 g (78% yield) of 2-fluoro-5-nitro-benzoic acid methyl ester 10-3 as a white powder; m/z=200 (M+H)+.

Aufarbeitung

  1. temperatureunder reflux during 16 h
  2. concentrationconcentrated
  3. filtrationthe resulting precipitate was filtered off
  4. washwashed with a small quantity of methanol

Quellen und Nachweise

ORD-Eintrag
ord-72d09bedf9c149588ed3642932685fcc
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524716B2

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