Hydrochloric Acid → HCID 70191672, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 28.2 g (0.150 mol) of 4-bromobenzylalcohol in 470 mL of dry dimethylformamide under nitrogen atmosphere was added 31.4 mL (0.225 mol) of triethylamine. The reaction mixture was cooled to 0° C. and 43 mL (0.17 mol) of t-butylchlorodiphenylsilane was added dropwise by addition funnel. The reaction mixture was stirred at ambient temperature overnight then poured into a separatory funnel containing 1 L of diethyl ether and 500 mL of water. To this mixture was added 125 mL of 2N aqueous hydrochloric acid. The layers were separated and the aqueous layer was extracted with diethyl ether (2×350 mL). The organic extracts were combined, washed with water (2×250 mL) and dried over magnesium sulfate. The solids were removed by filtration and the solvent removed under vacuum to give an oil which crystallized on standing. The flask containing the crude product was placed in the freezer overnight then triturated with a minimal amount of methanol and filtered. The solid was air dried for several hours then dried under vacuum overnight to afford 59.5 g (93%) of product as an off-white solid (mp 44-47° C.). 1H NMR (200 MHz, CDCl3): d 1.15 (s, 9 H), 4.76 (s, 2 H), 7.25 (d, 8 Hz, 2 H), 7.45 (m, 8 H), 7.75 (m, 4 H). FAB-MS: calculated for C23H25BrOSi 424; found 425 (M+H, 7%).

Provenance & Evidence