Reacción #605753

Ecuación de reacción

2,6-diiodo-4-methylsulfonylphenol

but-1-yne

→

title compound

Rendimiento 48.4%

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

Rendimiento 48.4%

Disolventes

pyridine

HCl

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe residue was cooled to 25° C.
2. 2
   Extracciónextracted with EtOAc (30 mL×2)
3. 3
   LavadoThe combined organic layers were washed by brine (100 mL)
4. 4
   Secadodried over Na2SO4
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated
7. 7
   OtroThe residue was purified by column chromatography (PE:EA=10:1 to 5:1)

Procedimiento

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+)

Fuente