Reaktion #51652

Reaktionsgleichung

4-acetamidophenol

(4-methoxycarbonylphenyl)boronic acid

→

methyl 4-(4-acetamidophenoxy)benzoate

Ausbeute 75.1%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeDry air
2. 2
   Sonstigefor 16 hours
3. 3
   Sonstigeat room temperature
4. 4
   EinengenThe resulting material is concentrated
5. 5
   Sonstigepurified by flash column chromatography (25-50% EtOAc in heptane)

Vorschrift

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.

Quelle