Sodium Hydroxide → 5-(2-Bromothiazol-5-yl)-2-fluorobenzonitrile

Participants

Reaction Steps

To a stirring solution of 2-fluoro-5-(thiazol-5-yl)benzonitrile THZ INT-3 (0.429 g, 2.1 mmol) in acetic acid (10.5 mL) was added potassium acetate (0.412 g, 4.2 mmol). Bromine (0.647 mL, 12.6 mmol) was added dropwise over 10 minutes and the reaction mixture stirred at room temperature for 48 h. The reaction mixture was basified with 1N NaOH and washed with EA and brine. The combined organic layers were dried over MgSO4, filtered, and concentrated. The crude product was purified by chromatography (20% EA/Hexanes) to produce 0.10 g (30%) of 5-(2-bromothiazol-5-yl)-2-fluorobenzonitrile THZ INT-4. LCMS-ESI (m/z) calculated for C10H4BrFN2S: 283.1; found 284.9 [M+H]+, tR=3.33 min.

Provenance & Evidence