3-(Bromomethyl)-5-fluoro-1-benzothiophene → 5-Fluoro-3-isobutyl-benzo[b]thiophene

HRID 1693137

Reaktionsgleichung

Reaktionsgleichung von HRID 1693137
Br[CH2:2][C:3]1[C:7]2[CH:8]=[C:9]([F:12])[CH:10]=[CH:11][C:6]=2[S:5][CH:4]=1.[CH:13]([Mg]Br)([CH3:15])[CH3:14]>C1COCC1>[F:12][C:9]1[CH:10]=[CH:11][C:6]2[S:5][CH:4]=[C:3]([CH2:2][CH:13]([CH3:15])[CH3:14])[C:7]=2[CH:8]=1

Komponenten

4

Edukt 2

HCID 136425923-(Bromomethyl)-5-fluoro-1-benzothiopheneHCID 178418365HCID 178418365, Verbindung

Produkt 1

HCID 597599805-Fluoro-3-isobutyl-benzo[b]thiophene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 3-bromomethyl-5-fluorobenzothiophene (2.0 g; cf. Raga, Manuel; Palacin, Celia; Castello, Josep Maria; Ortiz, Jose A.; Cuberes, Maria Rosa; Moreno-Manas, Marcial, Eur. J. Med. Chem. (1986), 21(4), 329-32) in THF (30 ml) was added over 5 minutes isopropylmagnesium bromide (1.0 M, 16.6 ml). The reaction mixture was stirred at 50° C. for 5 h, cooled, quenched with ice/water and ammonium chloride solution, and extracted with ethyl acetate. The organic phases were washed with water, dried and concentrated. The residue was chromatographed on silica gel using heptane/methylene chloride as eluent to obtain the title compound (1.35 g) as a yellowish oil. MS (EI): 208.3 (M)

Aufarbeitung

  1. temperaturecooled
  2. customquenched with ice/water and ammonium chloride solution
  3. extractionextracted with ethyl acetate
  4. washThe organic phases were washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-251515dd99554df396bb60853627d78e
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158655B2

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