1-Bromo-4-fluorobenzene → HCID 21090461, compound

Participants

Reaction Conditions

Reaction Steps

To a p-xylene (25 mL) solution containing 4-fluorobromobenzene (275 μL, 2.5 mmol, 1.0 eq), 4-N—BOC-aminopiperidine (1.0 g, 4.99 mmol, 2.0 eq), and potassium t-butoxide (393 mg, 3.5 mmol, 1.4 eq) was added palladium (II) acetate (6 mg, 1 mol %) and tri-t-butylphosphine (20 mg, 4 mol %). The resulting mixture was then heated to 120° C. for 4 h at which time it was poured into a sat. NaHCO3 solution and extracted (2×) with EtOAc. The combined extracts were dried over MgSO4 and concentrated in vacuo. The resulting oil was purified via column chromatography using 1:1 hexanes/EtOAc as the mobile phase. Isolated 485 mg (1.65 mmol, 67% yield).

Provenance & Evidence