Reacción #51652

Ecuación de reacción

4-acetamidophenol

(4-methoxycarbonylphenyl)boronic acid

→

methyl 4-(4-acetamidophenoxy)benzoate

Rendimiento 75.1%

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroDry air
2. 2
   Otrofor 16 hours
3. 3
   Otroat room temperature
4. 4
   ConcentraciónThe resulting material is concentrated
5. 5
   Otropurified by flash column chromatography (25-50% EtOAc in heptane)

Procedimiento

Dry air is bubbled through a solution of 4-acetamidophenol (320 mg, 2.1 mmol), copper(II) acetate (384 mg, 2.1 mmol), TEA (1.5 mL, 10.5 mol), (4-methoxycarbonylphenyl)boronic acid (760 mg, 4.2 mmol), and powdered molecular sieves (2 g) in CH2Cl2 (21 mL) for 16 hours at room temperature. The resulting material is concentrated and purified by flash column chromatography (25-50% EtOAc in heptane) to give methyl 4-(4-acetamidophenoxy)benzoate (450 mg, 75%). 1H NMR (300 MHz, DMSO) δ 8.01, 7.54, 7.27, 7.05, 6.98, 3.92, 2.22.

Fuente