5-Bromo-2-ethoxybenzaldehyde → HCID 12542423, compound

Participants

Reaction Conditions

Reaction Steps

Methyltriphenylphosphonium bromide (1.09 g, 3.05 mmol) was added to a solution of potassium t-butoxide (0.5 g, 2.29 mmol) in THF (8 mL). The resulting reaction mixture turned bright yellow and was stirred for 40 min after which, it was cooled to −78° C. 5-bromo-2-ethoxybenzaldehyde was dissolved in THF (2 mL) and added to the reaction which was stirred for 2 h. The reaction was warmed to rt, diluted with ether and filtered through celite. The filtrate was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. Silica gel chromatography eluting with 15% EtOAc/hexanes yielded 320 mg of the desired product: 1H NMR (500 MHZ, CDCl3) δ 7.58 (d, J=2.5 Hz, 1H), 7.31 (dd, J=6.4, 2.4 Hz, 1H), 6.96-7.04 (m, 1H), 6.74 (d, J=8.7 Hz, 1H), 5.77 (d, 1H), 5.32 (d, 1H), 4.03-4.07 (m, 2H), 1.45 (t, J=7.0 Hz, 3H).

Provenance & Evidence