Reaction #76761

Reaction equation

2-fluoro-4-chloro-5-isopropoxyphenylhydrazine

sodium acetate

water

1,1-dibromo-3,3,3-trifluoroacetone

→

3,3,3-trifluoro-2-oxo-propanal 1-(4-chloro-2-fluoro-5-isopropoxyphenylhydrazone)

Solvents

diethyl ether

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   OtherThe ether layer was separated
3. 3
   Washwashed once with 10 ml of saturated sodium chloride solution
4. 4
   Dryingdried with magnesium sulfate
5. 5
   workup.DISTILLATIONThe diethyl ether was distilled out

Procedure

To a mixed solution of 5.3 g (53.5 mmol) of sodium acetate and about 100 ml of water was added under ice cooling 6.6 g (24.3 mmol) of 1,1-dibromo-3,3,3-trifluoroacetone, and the reaction was allowed to proceed at 70° C. for 20 minutes. Then, the reaction mixture was cooled to room temperature, to which a solution of 5.8 g (21.5 mmol) of 2-fluoro-4-chloro-5-isopropoxyphenylhydrazine dissolved in about 20 ml of diethyl ether was added, and the reaction mixture was stirred at room temperature for 1 hour. The ether layer was separated, washed once with 10 ml of saturated sodium chloride solution, and dried with magnesium sulfate. The diethyl ether was distilled out, which afforded 6.5 g (20.0 mmol) of 3,3,3-trifluoro-2-oxo-propanal 1-(4-chloro-2-fluoro-5-isopropoxyphenylhydrazone).

Source