Dichloromethane → 2-tert-butyl-4-chloro-5-(2-fluoro-1-(4-tert-butylphenyl)-1-ethyl)oxy-3(2H)-pyridazinone

HRID 1516089Notes

Reaction equation

HRID 1516089 reaction equation
[C:1]([N:5]1[C:10](=[O:11])[C:9]([Cl:12])=[C:8]([O:13][CH:14]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:29][CH:28]=2)[CH2:15]OS(C2C=CC(C)=CC=2)(=O)=O)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[F-:37].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>O>[C:1]([N:5]1[C:10](=[O:11])[C:9]([Cl:12])=[C:8]([O:13][CH:14]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:29][CH:28]=2)[CH2:15][F:37])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 2724141Tetrabutylammonium FluorideHCID 866003922-tert-butyl-4-chloro-5-(2-p-toluenesulfonyloxy-1-(4-tert-butylphenyl)-1-ethyl)oxy-3(2H)-pyridazinone

Product 1

HCID 671001272-tert-butyl-4-chloro-5-(2-fluoro-1-(4-tert-butylphenyl)-1-ethyl)oxy-3(2H)-pyridazinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 15 ml round bottom flask charged with 2-tert-butyl-4-chloro-5-(2-p-toluenesulfonyloxy-1-(4-tert-butylphenyl)-1-ethyl)oxy-3(2H)-pyridazinone (0.2 g, 0.375 mmol) is added 3.75 ml of tetrabutylammonium fluoride solution (1M in THF, 3.75 mmol). The mixture is first stirred at room temperature for 15 minutes after which it is heated for 15 minutes at 100° C. The solution is then cooled to room temperature and to it is added dichloromethane followed by water. The layers were separated and the organic layer is washed with water and then dried. The organic layer is then concentrated and subjected to purification using silica gel flash chromatography (ethyl acetate/hexanes) to obtain the above compound.

Workup

  1. temperatureis heated for 15 minutes at 100° C
  2. temperatureThe solution is then cooled to room temperature and to it
  3. customThe layers were separated
  4. washthe organic layer is washed with water
  5. customdried
  6. concentrationThe organic layer is then concentrated
  7. customsubjected to purification
  8. customto obtain the above compound

Sources & evidence

ORD record
ord-07f37d8f5cd240c7ac32129796ddc8f9
Source dataset
uspto-grants-2012_07
Patent number
US08226929B2

Reaction notes

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