Imidazole → 1-Bromo-3-((((1,1-dimethylethyl)dimethylsilyl)oxy)methyl)benzene

Participants

Reaction Steps

To a 1-L round-bottomed flask were added 4-bromobenzyl alcohol (100.0 g, 0.53 mol), imidazole (91.0 g, 1.34 mol), t-butyldimethylsilyl chloride (TBDMS-Cl) (96.5 g, 0.64 mol), and DMF 100 mL. The reaction mixture was stirred at room temperature under nitrogen overnight. The reaction was poured into water and extracted with ether three times and the combined organic phase was washed with water three times and dried over MgSO4. After solvent was removed, the product was obtained as light yellow liquid 154 g (62% yield). 1H NMR (CDCl3) δ (Ppm): 0.07 (s, 9H), 0.91 (s, 6H), 4.65 (s, 2H), 7.17 (d, J=8.2 Hz, 2H), 7.42 (s, J=8.3 Hz, 2H); 13C NMR (CDCl3): −1.71, 21.93, 29.48, 67.89, 124.13, 131.27, 134.82, 144.02; FD-MS: m/z 301 (M+).

Provenance & Evidence