Phenol → 3-Chloro-6-phenoxypyridazine

HRID 1294677Notes

Reaction equation

HRID 1294677 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[C:9]1([OH:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>[OH-].[Na+]>[Cl:1][C:2]1[N:3]=[N:4][C:5]([O:15][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 996PhenolHCID 673313,6-Dichloropyridazine

Product 1

HCID 4034133-Chloro-6-phenoxypyridazine

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

3,6-Dichloropyridazine (Aldrich, 4.47 g, 30 mmol) in NaOH (10%, 20 mL) was treated with phenol (Aldrich, 1.88 g, 20 mmol) at 100° C. for 15 hours. After cooling to room temperature, the mixture was extracted with ethyl acetate (2×50 mL). The extracts were combined and concentrated under reduced pressure. The title compound was purified by chromatography (SiO2, Hexanes: ethyl acetate=80: 20, Rf. 0.5) as a solid (3.8 g, yield, 92%). 1H NMR (CDCl3, 300 MHz) δ 7.11–7.29 (m, 3H), 7.38–7.55 (m, 4H) ppm. MS (DCl/NH3) m/z 207 (M+H)+, 209 (M+H)+.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (2×50 mL)
  2. concentrationconcentrated under reduced pressure
  3. customThe title compound was purified by chromatography (SiO2, Hexanes: ethyl acetate=80: 20, Rf. 0.5) as a solid (3.8 g, yield, 92%)

Sources & evidence

ORD record
ord-54b584b693934dea97c38bf24c55873c
Source dataset
uspto-grants-2007_07
Patent number
US07241773B2

Reaction notes

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