Phenol → 3,6-Diphenoxypyridazine

HRID 1294678Notes

Reaction equation

HRID 1294678 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].Cl[C:15]1[N:16]=[N:17][C:18]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:19][CH:20]=1>O1CCCC1.C(OCC)(=O)C>[O:7]([C:15]1[N:16]=[N:17][C:18]([O:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[CH:19][CH:20]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 4034133-Chloro-6-phenoxypyridazineHCID 23665647Potassium tert-butoxide

Product 1

HCID 130263683,6-DiphenoxypyridazineYield 84%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Phenol (Aldrich, 1.88 g, 20 mmol) in tetrahydrofuran (50 mL) was treated with potassium tert-butoxide (Aldrich, 2.24 g, 20 mmol) at ambient temperature for 10 minutes. The product of Example 27A (3.0 g, 14.5 mmol) was then added and the reaction mixture was stirred at 60° C. for 10 hours. The mixture was allowed to cool to room temperature, diluted with ethyl acetate (100 mL), and washed with brine (2×10 mL). The organic phase was concentrated affording the title compound as a solid (3.2 g, yield, 84%). 1H NMR (MeOH-d4, 300 MHz) δ 7.14–7.28 (m, 6H), 7.38–7.48 (m, 6H) ppm. MS (DCl/NH3) m/z 265(M+H)+.

Workup

  1. temperatureto cool to room temperature
  2. washwashed with brine (2×10 mL)
  3. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-866ebdc663714dc8978d1f487d2b5cfe
Source dataset
uspto-grants-2007_07
Patent number
US07241773B2

Reaction notes

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