Imidazole → 3-(4-Bromophenyl)propoxy-tert-butyl-dimethylsilane

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Reaction Steps

A sol. of 3-(4-bromo-phenyl)-propan-1-ol (49.4 g, 230 mmol) in DMF (500 mL) is cooled to 0° C., and imidazole (23.77 g, 349 mmol) and TBDMS-Cl (52.6 g, 349 mmol) are added. The mixture is stirred overnight, while warming up to rt. The mixture is diluted with heptane (1.0 L) and aq. sat. NH4Cl (800 mL), and the mixture is shaken. The layers are separated. The aq. layer is extracted with heptane, and the combined org. extracts are washed with brine. The org. extracts are dried over MgSO4, filtered, and the solvents are removed under reduced pressure. Purification by FC (Et2O/heptane 1:99→1:19) yields the title compound (68.1 g, 90%). LC-MS: tR=1.24 min.

Provenance & Evidence