Dimethylformamide → 4-Bromo-1-naphthaldehyde

Participants

Reaction Steps

To a 150 ml flask was added 1,4-dibromonaphthalene (2.0 g, 7.0 mmol) and anhydrous ether (50 ml). After cooling to 0° C. n-BuLi (3.1 ml of 2.5 M in hexanes, 7.7 mmol) was added dropwise and stirred for 20 minutes after which anhydrous DMF (1.62 ml, 21 mmol) was added. The reaction was then warmed to ambient temperature and after 1 h the reaction was quenched with water (10 ml), stirred for 10 minutes, and extracted with ether (3×). The ether layer was dried over anhydrous Na2SO4, passed through a silica plug, and concentrated to afford 1.02 g (62%) of product as a pure off-white solid: 1H NMR (300 MHz, DMSO-d6): δ 7.80–7.85 (2H, m), 8.10 (1H, d, J=7.7 Hz), 8.20 (1H, d, J=7.7 Hz), 8.32 (1H, m). 9.24 (1H, m), 10.42 (1H, s).

Provenance & Evidence