Caprolactam → 1-(4-Fluorophenyl)azepan-2-one

Participants

Reaction Conditions

Reaction Steps

A suspension of ε-caprolactam (10 g, 90 mmol), 1-fluoro-4-iodobenzene (10 ml, 90 mmol), L-proline (4.1 g, 36 mmol), K2CO3 (37 g, 270 mmol), and Cu(I)I (3.4 g, 18 mmol) was stirred in DMSO (50 mL) and heated to 100° C. for 12 hours. Water (50 mL) was added and the reaction mixture was extracted with EtOAc. The organic layer washed with water) and brine, dried with Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography (50% EtOAc in hexane) to afford the product (1.2 g, 6.4% yield) as brown oil. LRMS (APCI pos) m/e 208.0 (M+1).

Provenance & Evidence