반응 #605753

반응 방정식

2,6-diiodo-4-methylsulfonylphenol

but-1-yne

→

title compound

수율 48.4%

2-ethyl-7-iodo-5-methylsulfonyl-1-benzofuran

수율 48.4%

용매

pyridine

HCl

반응 조건

후처리

1. 1
   온도The residue was cooled to 25° C.
2. 2
   추출extracted with EtOAc (30 mL×2)
3. 3
   세척The combined organic layers were washed by brine (100 mL)
4. 4
   건조dried over Na2SO4
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타The residue was purified by column chromatography (PE:EA=10:1 to 5:1)

실험 절차

To a solution of 2,6-diiodo-4-methylsulfonylphenol (1.00 g, 2.36 mmol) in pyridine (10 mL) at 25° C. was added but-1-yne (128 mg, 2.36 mmol) and Cu2O (135 mg, 0.944 mmol). The mixture was stirred at 130° C. for 3 h under a nitrogen atmosphere. The residue was cooled to 25° C., diluted with 1N HCl (200 ml) and extracted with EtOAc (30 mL×2). The combined organic layers were washed by brine (100 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography (PE:EA=10:1 to 5:1) to afford the title compound (400 mg, 48%) as a solid. 1H NMR (CDCl3, 400 MHz) δ 8.14 (d, J=1.6 Hz, 1H), 8.06 (d, J=1.6 Hz, 1H), 6.62 (s, 1H), 3.09 (s, 3H), 2.90 (q, J=7.6 Hz, 2H), 1.38 (t, J=7.6 Hz, 3H). LCMS: 350.9 (M+H+)

출처