تفاعل #51652

معادلة التفاعل

4-acetamidophenol

(4-methoxycarbonylphenyl)boronic acid

→

methyl 4-(4-acetamidophenoxy)benzoate

المردود 75.1%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   أخرىDry air
2. 2
   أخرىfor 16 hours
3. 3
   أخرىat room temperature
4. 4
   تركيزThe resulting material is concentrated
5. 5
   أخرىpurified by flash column chromatography (25-50% EtOAc in heptane)

الإجراء التجريبي

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.

المصدر