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

Participants

Reaction Conditions

Reaction Steps

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)

Provenance & Evidence