2-Bromo-4-methylpyridine → 4-Methyl-2-pentylpyridine

Participants

Reaction Conditions

Reaction Steps

A 50 ml reactor under argon was charged with 2-bromo-4-methylpyridine and THF. The reaction was cooled to −78° C. and the Pd(dppf)2Cl2 (dppf being 1,1′-di(diphenylphosphine)-ferrocene) catalyst was added, followed by 3.0 M pentyl magnesium bromide. The reaction was allowed to warm to 0° C. until the starting material was consumed. The reaction was quenched with 20 ml of saturated ammonium chloride solution and extracted with 20 ml of ethylacetate. The ethyl acetate layer was extracted with 20 ml of 1 M aqueous hydrochloric acid to extract the pyridine product from neutral organics. The aqueous acid layer was neutralized with 1 M NaOH and extracted with 20 ml of ethyl acetate. The ethyl acetate layer was washed with brine and dried on anhydrous sodium sulphate. The product phase was filtered and concentrated on the rotary evaporator to give 850 mg of product, a 44.9% yield.

Provenance & Evidence