(Diethylamino)sulfur trifluoride → N-[1-fluoromethyl-2-(2,4,6-trichloro-phenyl)-ethyl]-O-methylhydroxylamine

Participants

Reaction Conditions

Reaction Steps

To a stirred thick suspension of 2-methoxyamino-3-(2,4,6-trichloro-phenyl)-propan-1-ol (1.0 g; 3.5 mmol) in dichloromethane (7.0 ml) at −16° C. under nitrogen was added dropwise a solution of diethylaminosulfur trifluoride (0.46 ml; 3.5 mmol) in dichloromethane (2.0 ml). During addition temperature rose to −12° C. The mixture turned to a brown orange solution which was allowed to warm at 20° C. and was stirred for 2 h. The organic solution was washed with saturated hydrogen carbonate solution (gas release), 1N hydrochloric acid, brine and dried over sodium sulfate. The solvent was removed in vacuo. The crude material was subject to flash column chromatography (eluant: cyclohexan/ethyl acetate 95:5) to afford 0.43 g (43% of theory) of N-[1-fluoromethyl-2-(2,4,6-trichlorophenyl)-ethyl]-O-methyl-hydroxylamine as a yellow oil.

Provenance & Evidence