Pyrazole → 1-(4-Bromo-2-ethyl-benzyl)-1H-pyrazole

Participants

Reaction Conditions

Reaction Steps

A solution of pyrazole (616 mg, 9.1 mmol) in anhydrous DMF (30 mL) was treated with naH (60%, 362 mg). 4-Bromo-1-bromomethyl-2-ethyl-benzene (2.5 g, 9.1 mmol) was added and the resulting solution was stirred at 80° C. for 13 hours before it was cooled down to room temperature. The mixture was diluted with H2O, extracted with Et2O. The combined organic extracts were washed with H2O, brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography to afford the desired product (1.92 g, 80% yield). 1H NMR (300 MHz, CDCl3): δ 1.15 (t, J=7.5 Hz, 3 H), 2.59–2.66 (m, 2 H), 5.30 (s, 2 H), 6.26–6.28 (m, 1 H), 6.86–6.88 (m, 1 H), 7.29–7.32 (m, 2 H), 7.37–7.38 (m, 1 H), 7.54–7.55 (m, 1 H).

Provenance & Evidence