4-Bromoanisole → 2-(4-Methoxy-phenyl)-thiazole

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a solution of thiazole (3.0 g, 16 mmol) in THF (75 ml) was added n-BuLi (2.5 M in hexane, 11 ml, 27.3 mmol) at −78° C. dropwise, and stirred at −78° C. for 30 min. ZnCl2 (10.7 g, 78.3 mmol) was added at −78° C. in portions. The resulting mixture was stirred at −78° C. for 30 min, and room temperature for 1.5 h. To this solution was added 4-bromoanisole (1.60 g, 8.5 mmol) and terakis(triphenylphosphine)-palladium (0). The reaction mixture was heated to 65° C. for 16 h. After the catalyst was filtered off, the filtrate was concentrated in vacuo. The residue was purified by a column chromatography on silica gel with 25% ethyl acetate in hexane to yield the title product (2 g, 67%); 1H NMR (400 MHz, CDCl3) δ 7.90 (d, J=9.2 Hz, 2H), 7.81 (d, J=3.2 Hz, 1H), 7.25 (d, J=3.2 Hz, 1H), 6.95 (d, J=9.2 Hz, 2H), 3.86 (s, 3H); MS (ESI+) 192 (M+1, 100).

Herkunft & Nachweise