Acetyl bromide → 4-Bromo-2-ethylpyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-ethyl-4-nitro-pyridine (2.3 g, 15.1 mmol) and acetyl bromide (9 mL) were heated together at 75° C. for 16 hours. More acetyl bromide (10 mL) was added and the reaction was heated to 100° C. for 5 hrs. The reaction mixture was poured into ice, made basic with 20% NaOH and extracted with EtOAc. The organic extracts were washed with brine, dried over Na2SO4 and concentrated to a black oil. Purification by flash silica gel chromatography (0% to 25% EtOAc) gave the product as an oil (1.72 g, 62%). 1H NMR (400 MHz, CDCl3): δ 1.30 (t, J=7.6 Hz, 3 H), 2.81 (d, J=7.6 Hz, 2 H), 7.28 (dd, J=5.3, 1.8 Hz, 1 H), 7.35 (d, J=1.8 Hz, 1 H), 8.34 (d, J=5.3 Hz, 1 H).

Provenance & Evidence