Imidazole → 2-Bromo-6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]naphthalene

Participants

Reaction Steps

2-Bromo-6-hydroxynaphthalene (100.0 g, 0.45 mol) and imidazole (75.0 g, 1.10 mol) were dissolved in 300 mL of DMF. To this solution was added TBDMS-Cl (80.0 g, 0.53 mol). The reaction was stirred at room temperature under nitrogen overnight. The reaction was poured into water, and the precipitate was filtered, washed with water and cold ethanol. The crude product was recrystallized from ethanol to give 97.2 g of off-white crystals (64% yield). 1H NMR (CDCl3) δ ppm: 0.24 (s, 6H), 1.01 (s, 9H), 7.07 (dd, J1=8.8 Hz, J2=2.3 Hz, 1H), 7.14 (s, 1H), 7.45 (dd, J1=8.8 Hz, J2=2.3 Hz, 1H), 7.53 (d, J=8.8 Hz, 1H), 7.60 (d, J=8.8 Hz, 1H), 7.90 (s, 1H). 13C NMR (CDCl3) δ ppm: −4.34, 18.24, 25.68, 114.86, 117.26, 123.05, 128.29, 128.42, 129.39, 129.57, 130.24, 133.04. Mp 62-64° C. FD-MS: 337 (M+).

Provenance & Evidence