N-bromobutanimide → 1-Bromo-2-(bromomethyl)-3-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer and reflux condenser was charged with 1-bromo-2-methyl-3-nitrobenzene (6.86 g, 31.8 mmol) and carbon tetrachloride (40 mL) and heated to 80° C. N-bromo-succinimide (6.96 g, 39.1 mmol) and 2,2′-azobis(2-methylpropionitrile) (522 mg, 3.18 mmol) were added, and the reaction mixture was stirred at 80° C. for 16 h. After this time, the reaction mixture was cooled to room temperature and filtered, and the filter cake was washed with methylene chloride (20 mL). The filtrate was concentrated under reduced pressure to afford crude 114a (9.64 g, 103% crude yield) as a yellow oil, which was used directly in the next step: 1H NMR (500 MHz, CDCl3) δ 7.89-7.86 (m, 2H), 7.35 (t, 1H, J=8.0 Hz), 4.89 (s, 2H).

Provenance & Evidence