Hello!
I am doing a reaction where I am formylating and chlorinating a pyrimidine-4,6-diol using the Vilsmeier-Haack Reaction. Upon finishing my reflux reaction, I quickly have to quench the reaction but have noticed a significant amount of gas vapors come from my glassware upon transferring it to the ice in the beaker. Furthermore, as i continue with the work-up i noticed that my yield is significantly lower than what it should be. Is it possible that my product is decomposing in the exothermic reaction occurring during the quenching step?