Réaction #51652

Équation de réaction

4-acetamidophenol

(4-methoxycarbonylphenyl)boronic acid

→

methyl 4-(4-acetamidophenoxy)benzoate

Rendement 75.1%

Solvants

CH2Cl2

Conditions de réaction

Traitement

1. 1
   AutreDry air
2. 2
   Autrefor 16 hours
3. 3
   Autreat room temperature
4. 4
   ConcentrationThe resulting material is concentrated
5. 5
   Autrepurified by flash column chromatography (25-50% EtOAc in heptane)

Mode opératoire

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.

Source