2,6-Dimethylphenol → 6-Chloro-3-(2,6-dimethylphenoxy)pyridazine 1-oxide

268 mg (2.20 mmol) of 2,6-dimethylphenol, 1,4-dioxane (3 mL) and dimethylsulfoxide (3 mL) were mixed, 270 mg (2.41 mmol) of potassium tert-butoxide was added to the mixture in an ice bath, and the resulting mixture was stirred for 10 minutes. To the mixture was added 370 mg (2.24 mmol) of 3,6-dichloropyridazine 1-oxide, and the resulting mixture was stirred at room temperature for 10 hours and allowed to stand for 2 days. The reaction mixture was poured into ice-cold water, and extracted with ethyl acetate. The organic layers were combined, washed successively with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate, gradient) to obtain 350 mg (1.39 mmol, Yield: 63.1%) of 6-chloro-3-(2,6-dimethylphenoxy)pyridazine 1-oxide.

1. stirringthe resulting mixture was stirred at room temperature for 10 hours
2. waitto stand for 2 days
3. additionThe reaction mixture was poured into ice-cold water
4. extractionextracted with ethyl acetate
5. washwashed successively with water and brine
6. dry with materialdried over anhydrous sodium sulfate
7. customThe solvent was removed
8. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate, gradient)

ORD record

ord-a3b8aab620c84cbaa13c00cf416f4987

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07964531B2