Imidazole → HCID 46183083, compound

Participants

Reaction Steps

To a 0° C. mixture of 2-hydroxy-5-bromotoluene(48.63 g, 260 mmol), DMF (260 ml), imidazole (18.58 g, 273 mmol) is added t-butyldimethylsilyl chloride (41.15 g, 273 mol) in portions. After stirring for 30 m, the reaction is warmed to RT and stirred for 16 h. The reaction mixture is poured into ice/water (1.25 l) and extracted with Et2O. The organic layer is washed with water (2×100 ml), 1N NaOH (2×5 ml), water, brine, MgSO4 dried, concentrated, chromatographed (hex), and azeotroped with toluene to give the title compound as an oil (75.7 g, 97%)

Provenance & Evidence