반응 #719818

반응 방정식

3-bromo-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene 1-oxide

4-bromophenol

sodium hydride

→

3-(4-bromophenoxy)-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene 1-oxide

수율 87.0%

용매

DMF

반응 조건

후처리

1. 1
   온도The reaction was heated to 80° C. for 18 h
2. 2
   온도was cooled to room temperature
3. 3
   기타quenched with water
4. 4
   workup.ADDITIONdiluted with DCM
5. 5
   기타The organic phase was collected (phase separator)
6. 6
   농축concentrated in vacuo
7. 7
   기타to afford the crude product
8. 8
   기타The crude material was purified by column chromatography (SiO2, 0-60% EtOAc/Heptane)

실험 절차

To a solution of 4-bromophenol (469 mg, 2.71 mmol) in DMF (3 mL) was added sodium hydride (60% suspension in oil, 108 mg, 2.71 mmol), the resulting mixture was allowed to stir for 10 min at room temperature. To the solution was added 3-bromo-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene 1-oxide (900 mg, 2.46 mmol) as a solid. The reaction was heated to 80° C. for 18 h. Upon completing the reaction was cooled to room temperature, quenched with water and diluted with DCM. The organic phase was collected (phase separator) and concentrated in vacuo to afford the crude product. The crude material was purified by column chromatography (SiO2, 0-60% EtOAc/Heptane) to afford 3-(4-bromophenoxy)-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene 1-oxide (980 mg, 2.14 mmol, 87% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm==7.70-7.78 (m, 2 H), 7.53 (d, J=2.02 Hz, 1 H), 7.41 (d, J=8.59 Hz, 2 H), 6.90-7.06 (m, 6 H), 3.91 (s, 3 H), 3.83 (s, 3 H).

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