N-bromobutanimide → HCID 59282949, compound

Participants

Reaction Conditions

Reaction Steps

Tetrakis(triphenylphosphine) palladium(0) (0.439 g, 0.380 mmol) was added to a solution containing 2-chloro-4-fluoropyridine (1 g, 7.60 mmol) and tributyl(1-ethoxyvinyl)tin (2.59 ml, 7.60 mmol) in Toluene (15.21 ml). In a capped vial, the reaction was heated to 110° C. for overnight. LC/MS verified that the vinyl enolate intermediate formed. The reaction was cooled to room temperature, filtered thru a plug of Celite and the filtrate concentrated. The resulting residue was diluted with THF (20 mL) and water (2 mL). The reaction mixture was cooled to 0° C. and N-bromosuccinimide (1.624 g, 9.12 mmol) was added. The reaction was stirring for 1 hour and warmed to room temperature. The reaction was diluted with ethyl acetate and washed with water. Separated organics, dried with MgSO4, filtered and concentrated. Purified using Combiflash using 0% to 20% ethyl acetate in hexanes to afford 2-bromo-1-(4-fluoropyridin-2-yl)ethanone (1.4 g, 6.42 mmol, 84% yield) as a light purple oil. 1H NMR (CDCl3, 400 MHz), δ: 4.81 (s, 2H), 7.24 (m, 1H), 7.79 (m, 1H), 8.65 (m, 1H).

Provenance & Evidence