Ethyl Bromide → HCID 70983236, compound

Participants

Reaction Steps

4,5-Dichloroimidazole (1.23 g, 9 mmol) was dissolved into 27 mL of acetonitrile. Potassium hydroxide (0.61 g, 9.9 mmol) was added and the mixture was allowed to stir for 0.5 h. Bromoethane (0.66 mL, 9 mmol) was added and the solution was allowed to reflux overnight. The solution was filtered hot to remove a white precipitate (presumed to be KBr) and 2-bromomethylnaphthalene (1.98 g, 9 mmol) was added and the mixture was returned to reflux overnight. The mixture was then allowed to cool to room temperature, resulting in a white precipitate (0.3538, 10% yield). 1H NMR (500 MHz, DMSO-d6) 9.62 (1H, s, NCHN), 7.61 (4H, m, Ar), 7.58 (3H, m, Ar),), 5.66 (2H, s, NCH2), 4.27 (2H, q, NCH2), 1.47 (3H, t, CH3). MS: m/z=304.8 (theor for C16H15Cl2N2Br1=386.12).

Provenance & Evidence