Tri-o-tolylphosphine → HCID 21837219, compound

Participants

Reaction Steps

Into a 15 mL round-bottomed flask fitted with a reflux condensor, a magnetic stirring bar, and a nitrogen inlet was added 1 mL dry toluene followed by 0.016 g (0.09 mmol) PdCl2 and 0.055 g (0.18 mmol) tri-o-tolylphosphine. After stirring for 15 min, an additional 15 mL dry toluene was added followed by 0.33 g (1.8 mmol) 3-ethylbromobenzene, 0.41 g (2.2 mmol) 1-Boc-piperazine and 0.242 g (2.5 mmol) sodium t-butoxide. The reaction was heated to reflux for 18 hr, after which time TLC (20% EtOAc/Hexane) showed the formation of a new spot. The reaction was cooled, diluted with 50 mL of ether, filtered through a Celite pad, and extracted with 3×10 mL water and 1×15 mL brine. The organic phase was dried (Na2SO4), filtered and the solvent removed in vacuo to get the crude product, which was purified by passing through a 2" silica pad (1% to 4% EtOAc/Hexane) to yield 1-Boc-4-(3-ethylphenyl)piperazine.

Provenance & Evidence