Pyridine → Ethyl 3-phenoxybenzoate

HRID 1777572Notes

Reaction equation

HRID 1777572 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[O:1]([C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 24522Ethyl 3-hydroxybenzoateHCID 66827Phenylboronic Acid

Product 1

HCID 15674478Ethyl 3-phenoxybenzoateYield 76.4%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl 3-hydroxybenzoate (0.200 g; 1.20 mmol), benzeneboronic acid (0.294 g; 2.41 mmol), copper acetate (0.437 g; 2.41 mmol) and pyridine (0.195 mL; 2.42 mmol) in dichloromethane (8 mL) was stirred at room temperature overnight. The reaction mixture was filtered and concentrated in vacuo. The crude mixture was purified by flash chromatography on silica gel (eluent 5 to 35% ethyl acetate in heptane) to yield 0.222 g (76%) of the title compound as a colourless oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customThe crude mixture was purified by flash chromatography on silica gel (eluent 5 to 35% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-9f9a3550fa1e49998c10b88a455d4039
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

Loading…