N-bromobutanimide → HCID 86691501, compound

Participants

Reaction Conditions

Reaction Steps

A 75 mL pressure vessel was charged with 2-bromo-3-methyl-5-nitropyridine (540 mg, 2.49 mmol), N-bromo-succinimide (452 mg, 2.54 mmol), 1,1′-azobis(cyclohexanecarbonitrile) (61 mg, 0.25 mmol) and 25 mL CCl4, The vessel was closed with a rubber septum and thoroughly purged with Argon. The rubber septum was switched to a Teflon cap and the reaction mixture was stirred at 100° C. for 42 h. The mixture was cooled to RT, filtered to remove the succinimide byproduct, washed with CCl4 and concentrated under vacuum. The crude residue was purified by chromatography on silica gel (using a solvent gradient from 1% to 20% EtOAc in hexanes) in order to isolate the desired product as a yellow oil (316 mg; 74% yield based on the amount of recovered starting material), along with some dibromonated byproduct (142 mg) and unreacted starting material (228 mg).

Provenance & Evidence