Acetaminophen → Methyl 4-(4-acetamidophenoxy)benzoate

HRID 1017641Notes

Reaction equation

HRID 1017641 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[CH3:12][O:13][C:14]([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)=[O:15]>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:19]2[CH:20]=[CH:21][C:16]([C:14]([O:13][CH3:12])=[O:15])=[CH:17][CH:18]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 1983AcetaminophenHCID 27343694-Methoxycarbonylphenylboronic acid

Product 1

HCID 22573305Methyl 4-(4-acetamidophenoxy)benzoateYield 75.1%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

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 the desired product (450 mg, 75%). 1H NMR (300 MHz, DMSO) δ8.01, 7.54, 7.27, 7.05, 6.98, 3.92, 2.22.

Workup

  1. customDry air
  2. customfor 16 hours
  3. customat room temperature
  4. concentrationThe resulting material is concentrated
  5. custompurified by flash column chromatography (25-50% EtOAc in heptane)

Sources & evidence

ORD record
ord-7e3975b9f09c43cdaf16abbcf75cd8e3
Source dataset
uspto-grants-2002_11
Patent number
US06479510B2

Reaction notes

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