Reaktion #1780319

Reaktionsgleichung

3-bromomethyl-5-fluorobenzothiophene

isopropylmagnesium bromide

→

title compound

5-Fluoro-3-isobutyl-benzo[b]thiophene

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled
2. 2
   Sonstigequenched with ice/water and ammonium chloride solution
3. 3
   Extraktionextracted with ethyl acetate
4. 4
   WaschenThe organic phases were washed with water
5. 5
   Sonstigedried
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe residue was chromatographed on silica gel

Vorschrift

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)

Quelle