2-tert-Butyl-6-methylphenol → 3-(2-Tert-butyl-6-methylphenoxy)-6-chloropyridazine

HRID 2424290Notes

Reaction equation

HRID 2424290 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:6]=1[OH:12])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].Cl[N:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[NH:21]1>O1CCOCC1>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:6]=1[O:12][C:25]1[N:20]=[N:21][C:22]([Cl:26])=[CH:23][CH:24]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 166782-tert-Butyl-6-methylphenolHCID 22028949HCID 22028949, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 230138653-(2-Tert-butyl-6-methylphenoxy)-6-chloropyridazineYield 54.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

17.5 g (107 mmol) of 2-tert-butyl-6-methylphenol, 11.9 g (106 mmol) of potassium tert-butoxide and 1,4-dioxane (250 mL) were mixed, and the mixture was stirred at room temperature for 30 minutes. To the mixture was added 15.0 g (101 mmol) of 2,6-dichloropyridazine and the resulting mixture was stirred at 100° C. for 3 hours and 15 minutes. The reaction mixture was poured into ice water, and extracted with ethyl acetate. The organic layer was washed successively with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed, and the residue was crystallized form isopropyl ether to obtain 15.3 g (55.2 mmol, Yield: 54.6%) of 3-(2-tert-butyl-6-methylphenoxy)-6-chloropyridazine.

Workup

  1. stirringthe resulting mixture was stirred at 100° C. for 3 hours and 15 minutes
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed successively with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed
  6. customthe residue was crystallized form isopropyl ether

Sources & evidence

ORD record
ord-2a5de23cc2984a2bab1112c5ca6202bc
Source dataset
uspto-grants-2011_06
Patent number
US07964531B2

Reaction notes

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