Reacción #420031

Ecuación de reacción

6-methoxybenzo[b]thiophene

trimethylacetic acid

K2CO3

2-bromo-5-fluorotoluene

→

2-(4-fluoro-2-methylphenyl)-6-methoxybenzo[b]thiophene

Rendimiento 44.0%

Disolventes

DMA

DCM

water

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe organic layer was collected (phase separator)
2. 2
   Concentraciónconcentrated
3. 3
   Otroto afford the crude product
4. 4
   ConcentraciónThe crude material was concentrated onto to silica gel
5. 5
   Otropurified by column chromatography (SiO2, 100% Heptanes)

Procedimiento

To a 20 mL microwave vial, 6-methoxybenzo[b]thiophene (1 g, 6.09 mmol), 2-bromo-5-fluorotoluene (0.808 mL, 6.39 mmol), BrettPhos palladacycle (1st generation) (0.243 g, 0.304 mmol), trimethylacetic acid (1.866 g, 18.27 mmol), and K2CO3 (2.52 g, 18.27 mmol) were suspended in DMA (10 mL). The reaction was heated for 90 min at 150° C. under microwave radiation. The reaction mixture was diluted with DCM and water. The organic layer was collected (phase separator) and concentrated to afford the crude product. The crude material was concentrated onto to silica gel and purified by column chromatography (SiO2, 100% Heptanes) to afford 2-(4-fluoro-2-methylphenyl)-6-methoxybenzo[b]thiophene (730 mg, 2.68 mmol, 44% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm=7.69 (d, J=9.09 Hz, 1H), 7.43 (dd, J=6.06, 8.59 Hz, 1H), 7.35 (d, J=2.53 Hz, 1H), 7.14 (s, 1H), 7.00-7.10 (m, 2H), 6.90-7.00 (m, 1H), 3.92 (s, 3H), 2.47 (s, 3H).

Fuente