Bis(triphenylphosphanium) dibromide → HCID 59240053, compound

Participants

Reaction Steps

A dry 250 mL flask was charged with triphenylphosphonium dibromide (6.3 g, 14.9 mmol) and a solution of [2-(2-chlorophenyl)-5-trifluoromethyl-2H-pyrazol-3-yl]-methanol (3.54 g in 100 mL of CH2Cl2) was added portionwise. The reaction was stirred at room temperature for 2 h then was washed into a separatory funnel with water and CH2Cl2. The CH2Cl2 was separated, dried (MgSO4), and concentrated in vacuo. The crude bromide was purified by silica gel flash chromatography (Jones Flashmaster, 70 g Silica gel, gradient elution from 100% hexanes to 10% ethyl acetate over 30 minutes). Appropriate fractions were combined and concentrated in vacuo to afford 5-bromomethyl-1-(2-chlorophenyl)-3-trifluoromethyl-1H-pyrazole as a colorless oil, yield: 2.74 g (64% for both steps); 1H NMR (400 MHz, CDCl3): δ 7.35-7.55 (m, 4H), 6.70 (s, 1H), 4.21 (br s, 2H).

Provenance & Evidence