Triethylamine → Tert-butyl(2-chloro-5-methylphenoxy)dimethylsilane

Participants

Reaction Conditions

Reaction Steps

A solution containing 2-chloro-5-methylphenol 79 (3.50 g, 25 mmol), triethylamine (3.8 mL, 27 mmol), and DMAP (0.030 g, 0.25 mmol) in 50 mL of DMF was chilled to 0° C. under N2. A solution of tert-butylchlorodimethylsilane (3.9 g, 26 mmol) in 5 mL of DMF was added to the reaction mixture slowly via syringe over 5 min. The reaction was warmed to room temperature and stirred for 12 h. The mixture was diluted with ether and it was extracted with 2×1 N HCl, water, and then brine. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude material was purified by silica gel chromatography using a 5% to 30% gradient of EtOAc in hexanes as the eluant. The desired fractions were combined and concentrated to give tert-butyl(2-chloro-5-methylphenoxy)dimethylsilane 80 (6.15 g, 98% yield) as a colorless oil.

Provenance & Evidence