1-Bromo-4-fluorobenzene → (r)-1-(4-Fluorophenyl)-3-methylpiperazine

Participants

Reaction Steps

To a mixture of 1-bromo-4-fluorobenzene (5.0 g, 0.0285 mol), (R)-2-methylpiperazine (3.15 g, 0.0313 mol) and sodium-tert-butoxide (4 g, 0.042 mol) in dry toluene (100 mL) under nitrogen was added Pd(OAc)2 (0.25 g, 0.0011 mol) followed by BINAP (0.75 g, 0.0012 mol). The reaction mixture was then refluxed for 18 h and cooled down to rt. The reaction mixture was washed with water, dried over magnesium sulfate, filtrated and concentrated. Purification of the crude by chromatography on silica (chloroform:MeOH, 8:2) gave the title compound as a liquid (2.5 g, 46% yield). TLC: Rf=0.25 (Chloroform/MeOH: 9/1).

Provenance & Evidence