Imidazole → (2-(3-Bromobenzyloxy)ethoxy)(tert-butyl)dimethylsilane

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[CH2:5][O:6][CH2:7][CH2:8][OH:9].N1C=CN=C1.[C:18]([Si:22]([CH3:25])([CH3:24])Cl)([CH3:21])([CH3:20])[CH3:19]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[CH2:5][O:6][CH2:7][CH2:8][O:9][Si:22]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:25])[CH3:24]

Participants

Procedure

A solution of 2-(3-bromobenzyloxy)ethanol [Aromatic Intermediate 25, step a] (3 g), imidazole (2.2 g) and tert-butyldimethylchlorosilane (2.2 g) in DCM (50 mL) was stirred at RT for 17 hours. The reaction mixture was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate (×2). The combined organic phases were dried and evaporated in vacuo. The crude product was purified by silica gel chromatography, gradient elution 10 to 40% ethyl acetate in isohexane. Fractions containing the product were evaporated to dryness to afford the subtitled compound as a colourless oil. Yield 3.8 g.