N,N,N',N'-Tetramethylethylenediamine → Diethyl 2,2-difluoropentanedioate

Participants

Reaction Steps

Commercially available ethyl bromodifluoroacetate (16 mL, 120 mmol) and ethyl acrylate (11 mL, 100 mmol) were dissolved in tetrahydrofuran (100 mL), and copper powder (15.2 g, 240 mmol) and TMEDA (16.7 mL, 110 mmol) were sequentially added thereto at room temperature. After stirring for about 8 hours, the reaction was terminated by the addition of a saturated aqueous solution of 1.0 N hydrochloric acid and was extracted two times with toluene. The reaction solution was distilled under reduced pressure and the concentrated title compound was directly used in the subsequent step without further purification.

Provenance & Evidence