Reaction #2286295

Reaction equation

2-[3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-ethanol

2-[3,5-Dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-ethanol

Jones Reagent

→

[3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-acetic acid

Yield 95.0%

[3,5-Dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-acetic acid

Yield 95.0%

Solvents

acetone

Conditions

Workup

1. 1
   Otherprepared via standard method) slowly dropwise at −4° C
2. 2
   OtherThe red reaction mixture
3. 3
   Otherwas quenched with isopropanol
4. 4
   FiltrationThe resulting green suspension was filtered through celite
5. 5
   Washthe celite was washed well with ethyl acetate (600 mL)
6. 6
   WashThe filtrate was washed with water (600 mL)
7. 7
   OtherThe organic layer was separated
8. 8
   Dryingdried with magnesium sulfate
9. 9
   Filtrationfiltered
10. 10
    Concentrationconcentrated
11. 11
    OtherThe resulting solid was dried under vacuum overnight

Procedure

A solution of 2-[3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-ethanol (17) (8.4 g, 23.2 mmol) in acetone (270 mL) was treated with Jones Reagent (34.8 mL of a 2.7 M solution, prepared via standard method) slowly dropwise at −4° C. The resulting red reaction mixture was stirred for 1 h at −3 to 0° C. The red reaction mixture was quenched with isopropanol. The resulting green suspension was filtered through celite and the celite was washed well with ethyl acetate (600 mL). The filtrate was washed with water (600 mL) and a saturated aqueous sodium chloride solution (300 mL). The organic layer was separated, dried with magnesium sulfate, filtered, and concentrated. The resulting solid was dried under vacuum overnight to afford [3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-acetic acid (18) (8.3 g, 95%) as a white solid; LRMS for C15H15Cl3N2O3 (M+) m/z=377. Molecular Weight=377.6574; Exact Mass=376.0148

Source