Triethylamine → 3-[[Dimethyl(1,1,2-trimethylpropyl)silyl]oxy]benzene bromide

Participants

Reaction Steps

To a stirred solution of 3-bromophenyl alcohol (5.0 g, 26.7 mmol) and triethylamine (3.25 g, 32.1 mmol) in anhydrous CH2Cl2 (125 mL) at room temperature under argon was added dropwise dimethylthexylsilylchloride (5.26 g, 29.4 mmol). After 1.5 hours, 4-dimethylaminopyridine (0.50 g) was added and the stirring was continued for an additional 3 hours. The reaction mixture was diluted with hexane (200 mL) and the precipitate was filtered off. The filtrate was concentrated, partitioned between hexane (200 mL) and 1N aqueous HCl (3×40 mL), and the organic layer was washed with saturated aqueous NaHCO3 (2×40 mL). The organic layer was dried (MgSO4), filtered and concentrated to yield title bromide (8.01 g, 91%).

Provenance & Evidence