Imidazole → HCID 58968658, compound

Participants

Reaction Steps

To a solution of (2-bromo-5-(trifluoromethyl)phenyl)methanol (10 g; 39 mmol) in N,N-dimethylformamide (100 mL) was added imidazole (6.82 g; 100.1 mmol) and triisopropylsilyl chloride (9.6 mL; 55.2 mmol) under N2. The reaction was stirred at room temperature for 48 hours. The reaction was diluted with ethyl acetate and washed with water (4×) and brine. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by 80 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 5-10% ethyl acetate in heptane) to yield the title compound (16.47 g, 100%) as a colorless oil. MS (GC) Calc: 410.0, Found: 391 (M−F). 1H NMR (400 MHz, CDCl3) δ ppm 7.94 (s, 1H), 7.62 (d, J=8.30 Hz, 1H), 7.39 (d, J=8.30 Hz, 1H), 4.84 (s, 2H), 1.25 (m, 3H), 1.12(d, 18H).

Provenance & Evidence