Reaction #51652

Reaction equation

4-acetamidophenol

(4-methoxycarbonylphenyl)boronic acid

→

methyl 4-(4-acetamidophenoxy)benzoate

Yield 75.1%

Solvents

CH2Cl2

Conditions

Workup

1. 1
   OtherDry air
2. 2
   Otherfor 16 hours
3. 3
   Otherat room temperature
4. 4
   ConcentrationThe resulting material is concentrated
5. 5
   Otherpurified by flash column chromatography (25-50% EtOAc in heptane)

Procedure

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