Reaction #64208

Reaction equation

2-(2,6-difluorophenyl)-4-methanesulfonyloxymethyl-2-oxazoline

4-(4-chlorophenyl)phenol

sodium hydroxide

ammonium chloride

→

2-(2,6-difluorophenyl)-4-{[4-(4-chlorophenyl) phenoxy]methyl}-2-oxazoline

Yield 18.2%

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   Extractionextracted twice with ethyl acetate
2. 2
   DryingThe residue was dried over magnesium sulfate
3. 3
   Concentrationconcentrated under reduced pressure

Procedure

A mixture of 200 mg (0.687 mmol.) of 2-(2,6-difluorophenyl)-4-methanesulfonyloxymethyl-2-oxazoline, 232 mg (1.00 mmol.) of 4-(4-chlorophenyl)phenol, 24 mg (1.0 mmol.) of sodium hydroxide and 3 ml of N,N-dimethylformamide was stirred at room temperature for 24 hours. After the reaction was completed, the reaction mixture was poured into 50 ml of a 10% aqueous solution of ammonium chloride and extracted twice with ethyl acetate. The residue was dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to give 50 mg of 2-(2,6-difluorophenyl)-4-{[4-(4-chlorophenyl) phenoxy]methyl}-2-oxazoline as a white solid (m.g. 99.5° C.).

Source