3-Bromopyridine → HCID 24822234, compound

Participants

Reaction Steps

In a 1 liter, 4 neck round bottom flask stirring under N2 was charged 80.6 milliliters (ml) of n-BuLi (1.55 Molar (M) solution, 0.125 moles, 1.25 equivalents (eq.)) to 300 ml of ether with stirring at -78° C. To the reaction was added, dropwise, 15.8 grams (g) of 3-bromopyridine (0.10 moles, 1.0 eq.) in 100 ml of ether, over 20 minutes while maintaining the temperature between -50° C. and -70° C. After stirring for 20 minutes, 21.3 g of chlorodimethylphenylsilane (0.125 moles, 1.25 eq.) in 50 ml of ether was added dropwise maintaining the temperature below -50° C. after which the reaction was allowed to come to ambient temperature. After 1 hour, gas liquid chromatography (GLC) indicated complete consumption of the silyl chloride. The reaction mixture was stirred overnight at room temperature. The reaction was quenched by adding 200 ml of water, and extracted with ether/ethyl acetate (200 ml/450 ml) and washed with water (2×200 ml). Drying and concentrating afforded 26.0 g of crude product of which 6.7 g was purified by flash chromatography with 3:7 ethyl acetate/hexane and afforded 2.1 g of an oil (31.2% yield based on the 6.7 g chromatographed portion).

Provenance & Evidence