Sodium Thiosulfate → 3-Bromo-5-(trifluoromethyl)pyridin-2-amine

Participants

Reaction Steps

To a mixture of 5-trifluoromethyl-pyridine-2-ylamine (65 g) and chloroform (100 mL), N-bromosuccinimide (71 g) was added in 5 parts under ice-cooling. The mixture was heated to room temperature, and stirred for 1 hour, then heated to 80° C., and stirred with heating for 30 minutes. After the mixture was allowed to cool to room temperature, into the mixture, saturated aqueous sodium thiosulfate solution and saturated aqueous sodium hydrogen carbonate solution were poured, and extracted with chloroform. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 96 g of 3-bromo-5-trifluoromethyl-pyridine-2-ylamine.

Provenance & Evidence