tert-Butanol → 4-[2-(4-Bromo-phenyl)-vinyl]-nicotinic acid

Participants

Reaction Conditions

Reaction Steps

0.9 g (22.5 mmol) of a 60% suspension of sodium hydride in paraffin are added to a solution of 2.25 g (30.40 mmol) of tertbutanol in 27.5 ml of DMF. The whole is heated in a water bath for 30′ till the evolution of hydrogen ends. The system is cooled at 0° C. and 2.5 g (15.13 mmol) of ethyl 4-methylnicotinate in 2.5 ml of DMF are dropped with stirring. After 1.5 hr stirring at the same temperature, 3.4 g (18.37 mmol) of 4-bromobenzaldehyde in 2.5 ml DMF are dropped. The system is stirred at room temperature overnight. The solution is poured over 100 g of ice and is filtered. The filtrate is acidified with acetic acid and the solid is filtered, washed with water and dried, yielding 1.85 g (40%) of a product that is used directly in the next step.

Provenance & Evidence