Imidazole → (3-Bromopropoxy)(tert-butyl)dimethylsilane

Participants

Reaction Steps

A modified procedure of Galka et al. (J. Lab. Comp. Rad. 2005, 48(11): 797-809) was used to prepare the title compound. A mixture of 3-bromopropanol (39.1 mmole; 5.43 g), tert.-butyldimethylsilylchloride (43.2 mmole; 6.47 g) and imidazole (46.7 mmole; 3.20 g) was stirred at RT for 3 hours under inert gas. The reaction was quenched with water, extracted with diethylether, the organic layer dried over MgSO4, filtered and concentrated. The purification was achieved by column chromatography (PE) to yield the title compound (36.4 mmole; 93%). 1H NMR (300 MHz, CDCl3) 3.73 (t; 3J=5.7 Hz; 2H; CH2O); 3.51 (t; 3J=6.4 Hz; 2H; CH2Br); 2.02 (q; 3J=5.7 Hz; 3J=6.4 Hz; 2H; CH2CH2CH2); 0.89 (s; 9H; C(CH3)3); 0.06 (s; 6H; 2×CH3).

Provenance & Evidence