Pyridine → Methyl 4-phenoxybenzoate

HRID 1777568Notes

Reaction equation

HRID 1777568 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[O:1]([C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 7456MethylparabenHCID 66827Phenylboronic Acid

Product 1

HCID 607605Methyl 4-phenoxybenzoate

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl 4-hydroxybenzoate (0.200 g; 1.31 mmol), benzeneboronic acid (0.321 g; 2.63 mmol), copper acetate (0.477 g; 2.63 mmol) and pyridine (0.213 mL; 2.63 mmol) in dichloromethane (8 mL) was stirred at room temperature overnight. The reaction mixture was filtered and concentrated in vacuo.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9ad4b59d447d4442bef54052f43b1b44
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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