Phenol → 2-Chloro-6-phenoxypyridine

HRID 2415171

Reaction equation

HRID 2415171 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[C:9]1([OH:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[Na+]>O>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([O:15][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 14798Sodium Hydroxide2×HCID 169892,6-Dichloropyridine

Product 1

HCID 8176622-Chloro-6-phenoxypyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A reaction mixture consisting of 1.48 g (10 mmol) of 2,6-dichloropyridine, 6 g (63.75 mmol) of phenol and 2.4 g (60 mmol) of sodium hydroxide in 10 ml of water is heated to 140° C. for 24 hours in a bomb. After cooling the reaction mixture is made strongly alkaline with sodium hydroxide solution and extracted with dichloromethane. The organic phase is separated off and dried over sodium sulphate. Purification is by column chromatography on silica gel (eluant: cyclohexane/ethyl acetate=3:1).

Workup

  1. temperatureAfter cooling the reaction mixture
  2. extractionextracted with dichloromethane
  3. customThe organic phase is separated off
  4. dry with materialdried over sodium sulphate
  5. customPurification

Sources & evidence

ORD record
ord-ac707bb3264f428cb065a83624731042
Source dataset
uspto-grants-2004_11
Patent number
US06818644B1

Linked notes

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