Pyridine → HCID 20755520, compound

HRID 916676Notes

Reaction equation

HRID 916676 reaction equation
C[C:2]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[F:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.N1C=CC=C[CH:23]=1>ClCCl>[CH3:23][O:6][C:4](=[O:5])[C:3]1[CH:7]=[CH:8][CH:9]=[C:10]([O:11][C:17]2[CH:16]=[CH:15][CH:14]=[C:13]([F:12])[CH:18]=2)[CH:2]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 2520233-Hydroxy-2-methylbenzoic AcidHCID 27339863-Fluorophenylboronic acid

Product 1

HCID 20755520HCID 20755520, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of methyl 3-hydroxybenzoic acid (5.4 g, 35.5 mmol), 3-fluorophenylboronic acid (5.5 g, 35.5 mmol), cupric acetate (7.1 g, 35.5 mmol), 3 A molecular sieves (9 g), pyridine (12 mL, 145 mmol) in dichloromethane (220 mL) was stirred at ambient temperature under ambient atmosphere. After 11 days, the mixture was filtered through Celite® and the volatiles were removed from the filtrate. The 3-(3-fluorophenoxy)benzoic acid methyl ester (3.68 g) was eluted from silica gel column with 5:1 hexane:ethyl acetate and taken onto the next step.

Workup

  1. filtrationthe mixture was filtered through Celite®
  2. customthe volatiles were removed from the filtrate
  3. washThe 3-(3-fluorophenoxy)benzoic acid methyl ester (3.68 g) was eluted from silica gel column with 5:1 hexane

Sources & evidence

ORD record
ord-4c7a841886184d778a18120479341c16
Source dataset
uspto-grants-2007_09
Patent number
US07271183B2

Reaction notes

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