Triethylamine → (2-Bromoethyl)phosphonochloridic acid

Participants

Reaction Conditions

Reaction Steps

(2-Bromoethyl)phosphonic acid monochloride was prepared from phosphorous pentachloride and (2-bromoethyl)phosphonic acid according to E. Baer and N. Z. Stanacey, J. BIOL. CHEM., 10: 3754 (1965). A portion of this reagent was dissolved in about 50 ml of anhydrous, ethanol-free chloroform, cooled in an ice-water bath to about 10° C. To this was added a portion of 2-(benzyloxy)-3-(octadecyloxy)-1-propanol and about 3.0 ml of dry triethylamine in about 50 ml of dry chloroform, under argon, with stirring over a period of one hour. The reaction was allowed to stand at room temperature about 48 hours, then was refrigerated at about 0° C. overnight and then taken to dryness. The residue was dissolved in toluene, filtered and the filtrate taken to dryness. The residue was extracted with ether, giving the desired title compound as a pale yellow syrup.

Provenance & Evidence