Diethyl chlorophosphate → Diethyl ((phenylsulfonyl)methyl)phosphonate

Participants

Reaction Conditions

Reaction Steps

A stirred solution of methyl phenyl sulfone (20 g, 0.128 mol) in dry THF (200 mL) was cooled at −78° C. in an acetone/dry ice bath. Lithium bis(trimethylsilyl)amide (Li HMDS; 134 mL, 1 M solution in THF, 0.134 mol) was added dropwise over 1 h. The resulting white suspension was stirred for an additional hour at −78° C. and diethyl chlorophosphate (18.5 mL, 128 mmol) in THF (20 mL) was added. The reaction mixture was stirred at −78° C. for 0.5 h, then allowed to slowly warm to room temperature and left stirring for 4 h. The reaction mixture was next concentrated under reduced pressure, the residue was dissolved in EA (500 mL), washed with brine (100 mL),dried over anhydrous Na2CO3 and concentrated under reduced pressure. The resultant crude material was purified by flash chromatography on silica gel (EA:H, 3:1 to 1:1) to afford the desired product as white solid (17.9 g, 48%).

Provenance & Evidence