Reaction #792139

Reaction equation

sodium hydride

trimethylsulfonium iodide

1-[2-chloro-4-(4-chlorophenoxy)phenyl]propan-1-one

→

2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-ethyl-oxirane

Yield 107.5%

Solvents

THF

DMSO

DMSO

DMSO

Conditions

Workup

1. 1
   TemperatureThe resulting mixture was then warmed to room temperature overnight
2. 2
   Otherquenched with an aqueous solution of ammonium chloride and iced water
3. 3
   Extractionextracted with MTBE
4. 4
   WashThe organic solvents were washed with water
5. 5
   Otherdried
6. 6
   Otherevaporated

Procedure

To a solution of sodium hydride (35.72 g, 1.49 mol) in THF (1 L) and dry DMSO (2 L) was added under argon drop wise at 5° C. a solution of trimethylsulfonium iodide (290.5 g, 1.42 mol) in dry DMSO (2 L). The mixture was stirred 1 hour at 5° C. followed by a dropwise addition of 1-[2-chloro-4-(4-chlorophenoxy)phenyl]propan-1-one (199.0 g, 0.65 mol) in DMSO (500 mL). The resulting mixture was then warmed to room temperature overnight and quenched with an aqueous solution of ammonium chloride and iced water, and then extracted with MTBE. The organic solvents were washed with water, dried and evaporated to give 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-ethyl-oxirane as a yellowish solid (216.0 g, 97%). 1H-NMR (CDCl3; 400 MHz) • • (ppm)=0.9 (t, 3H); 1.75 (m, 1H); 2.10 (m, 1H); 2.80 (d, 1H); 3.05 (d, 1H); 6.85 (d, 1H); 6.95 (m, 3H); 7.30 (d, 2H); 7.40 (d, 1H).

Source