Réaction #1041

Équation de réaction

i-propanol

4-bromo-3-chloro-3,4,4-trifluorobutanol

Jones reagent

→

4-bromo-3-chloro-3,4,4-trifluorobutanoic acid

Rendement 85.0%

4-bromo-3-chloro-3,4,4-trifiuorobutanoic acid

Rendement 85.0%

Solvants

methylene chloride

acetone

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGThe mixture was then stirred at room temperature for 30 min
2. 2
   AutreThe precipitated salts were removed by filtration
3. 3
   Lavagewashed with acetone
4. 4
   AutreThe residue obtained after concentration of the flitrate
5. 5
   Lavagewashed with 1N HCl (50 mL), brine
6. 6
   Séchagedried over anhydrous magnesinm sulfate
7. 7
   AutreEvaporation of the solvent

Mode opératoire

A solution of 4-bromo-3-chloro-3,4,4-trifluorobutanol (IX) (2.41 g, 10 mmol) in acetone (35 mL) was treated with Jones reagent (7.5 mL) in 10 min with stirring and cooling (ice-water bath). The mixture was then stirred at room temperature for 30 min and 0.5 mL of i-propanol was then added. The precipitated salts were removed by filtration, washed with acetone. The residue obtained after concentration of the flitrate was dissolved in methylene chloride (100 mL), washed with 1N HCl (50 mL), brine, and dried over anhydrous magnesinm sulfate. Evaporation of the solvent gave 2.17 g (85%) of 4-bromo-3-chloro-3,4,4-trifluorobutanoic acid (VIII) as a clear oil.

Source