2-Methyl-5-hydroxypyridine → HCID 23335279, compound

Participants

Reaction Conditions

Reaction Steps

4 g of a potassium salt of 5-hydroxy-2-methylpyridine was suspended in 10 ml of dimethylformamide, and 6.15 g of p-bromobenzotrifluoride and 500 mg of a copper powder were added to the suspension, followed by stirring in a nitrogen stream at 125° C. for 18 hours to effect the reaction. The reaction mixture was allowed to cool, diluted with 50 ml of methanol and then filtered. The filtrate was immediately dried to a solid, and 150 ml of chloroform and 100 ml of water were added to the residue. The resulting mixture was adjusted to a pH of 9.5 with 5 N sodium hydroxide and any insoluble matter again separated by filtration. The chloroform layer was dried with anhydrous sodium sulfate and immediately concentrated to dryness to obtain 5.6 g of oily 5-(p-trifluoromethylphenoxy)-2-methylpyridine.

Provenance & Evidence