반응 #420031

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6-methoxybenzo[b]thiophene

trimethylacetic acid

K2CO3

2-bromo-5-fluorotoluene

→

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

수율 44.0%

용매

DMA

DCM

water

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후처리

1. 1
   기타The organic layer was collected (phase separator)
2. 2
   농축concentrated
3. 3
   기타to afford the crude product
4. 4
   농축The crude material was concentrated onto to silica gel
5. 5
   기타purified by column chromatography (SiO2, 100% Heptanes)

실험 절차

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).

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