Pyridine → Methyl 4-(3-fluorophenoxy)benzoate

HRID 1777578Notes

Reaction equation

HRID 1777578 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.[F:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:12][C:13]1[CH:18]=[C:17]([CH:16]=[CH:15][CH:14]=1)[O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 7456MethylparabenHCID 27339863-Fluorophenylboronic acid

Product 1

HCID 67973924Methyl 4-(3-fluorophenoxy)benzoate

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl 4-hydroxybenzoate (0.400 g; 2.63 mmol), 3-fluorobenzene boronic acid (0.735 g; 5.26 mmol), copper acetate (0.955 g; 5.26 mmol) and pyridine (0.425 mL; 5.26 mmol) in dichloromethane (15 mL) was stirred at room temperature overnight. The reaction mixture was filtered and concentrated under reduced pressure.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cb1f2ccb3941421198d896d3ed1b911d
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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