Hydrochloric Acid → 2-Methoxy-5-(trifluoromethyl)nicotinaldehyde

Participants

Reaction Conditions

Reaction Steps

A solution of 5.18 g (0.020 mol) of 3-bromo-2-methoxy-5-(trifluoromethyl)pyridine in 50 ml of ether was cooled to -100° C. and blanketed with nitrogen. A solution containing 0.024 mole of butyl lithium in hexane (15.0 ml of 1.6 M) was added slowly with stirring keeping the temperature below about -95° C. and the mixture was allowed to react for another 15 min. Dimethylformamide (7.5 ml, 0.097 mol) was added to the mixture at below -95° C. and stirring continued for about 30 min. The mixture was allowed to warm to about 20° C. and was then poured onto a mixture of ice and 1N hydrochloric acid. The mixture that formed was extracted with ether and the extract was dried over sodium sulfate and concentrated by evaporation under reduced pressure. The residue was distilled in a Kugelrohr apparatus to obtain 3.6 g (86 percent of theory) of the title compound as an oil which solidified to a white crystalline solid. The proton nmr spectrum was consistent with the assigned structure.

Provenance & Evidence