Diethyl chlorophosphate → HCID 87097481, compound

Participants

Reaction Conditions

Reaction Steps

To a 250-mL round-bottom flask equipped with a magnetic stir bar was added 2′-bromo-2,6-dimethoxybiphenyl (see Buchwald SL, Journal of the American Chemical Society 2005;127:4685-4696)(7.02 g, 24.0 mmol, 1 equiv). Degassed, anhydrous tetrahydrofuran was added (80 mL) followed by N,N,N′,N′-tetramethylethylene-1,2-diamine (4.31 mL, 28.7 mmol, 1.2 equiv). The resulting solution was cooled to −78 ° C., and then n-butyllithium (11.5 mL, 28.7 mmol, 1.2 equiv, 2.5 M hexanes) was added in a dropwise fashion. After the addition of 5 mL of n-butyllithium the reaction slurry could no longer be stirred. The reaction flask was warmed to 0 ° C. at which point the slurry became free-flowing. The remainder of the n-butyllithium (˜6.5 mL) was added over the course of 10 minutes. The reaction was stirred for 90 minutes at 0 ° C., and then the aryllithium intermediate was quenched with diethyl chlorophosphate (4.15 mL, 28.7 mmol, 1.2 equiv).

Provenance & Evidence