Hydrochloric Acid → HCID 89782106, compound

Participants

Reaction Steps

A solution of 8-bromo-2-fluoroquinoxaline (2.36 g, 10.39 mmol), tributyl(1-ethoxyvinyl)stannane (3.86 ml, 11.43 mmol; Aldrich), and Pd(PPh3)4 (0.360 g, 0.312 mmol) in toluene (74 ml) and THF (29 ml) was heated to reflux for 1.5 h. The reaction mixture was cooled to RT before conc. HCl (1.083 ml, 12.99 mmol) was added to convert the silyl enol ether to the methyl ketone. After stirring for 5 min, Et3N (3.62 ml, 26.0 mmol) was added to quench the HCl. The crude material was concentrated, taken up in DCM, adsorbed onto silica, and purified via automated flash chromatography (silica gel) with 100% hexanes to 60% DCM in hexanes to give 1-(3-fluoroquinoxalin-5-yl)ethanone (210 g, 87% yield) as a pale yellow solid. MS (ESI, pos. ion) m/z: 191.0 (M+1).

Provenance & Evidence