Phenol → HCID 54284133, compound

Participants

Reaction Conditions

Reaction Steps

A solution of phenol (2.68 g, 0.0285 mole) and triethylamine (3.97 ml, 0.0285 mole) in 50 ml. of ether was added to a solution of ethyl N-trifluoroacetyl-N-(dichlorophosphonomethyl)glycinate (9.9 g, 0.03 mole) in 175 ml. of ether at 0° C. After three hours, the reaction mixture was filtered and the cooled (0° C.) filtrate was treated with a solution of ethanethiol (2.13 ml, 0.0285 mole) and triethylamine (3.97 ml, 0.0285 mole) in 50 ml. of ether. After stirring at 25° C. overnight, the solution was filtered and the filtrate was washed with 1.5% hydrochloric acid, 1.5% ammonium hydroxide and saturated sodium chloride solution. Concentration in vacuo afforded an oil which was chromatographed on silica gel eluting with ethyl acetate/cyclohexane (1:1) to yield ethyl N-trifluoroacetyl-N-(phenoxy(ethylthio)phosphonomethyl)glycinate (1.5 g) as a clear oil, ND25 =1.4969.

Provenance & Evidence