Phenyl Isothiocyanate → HCID 66820810, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (trimethylsilyl)diazomethane in hexane (2M, 1.74 mL, 3.5 mmol) in tetrahydrofuran (10 mL) at −78° C. was added dropwise n-BuLi and the mixture was stirred at −78° C. for 1 hour. Isothiocyanatobenzene (500 mg, 2.9 mmol) in THF (4 mL) was added and the mixture was stirred at −78° C. for 1 hour. Ethyl bromoacetate (484 mg, 2.9 mmol) was then added and the mixture was stirred at −78° C. for 30 min. and then at 0° C. for additional 30 min. Iced water was added to the reaction and the mixture was extracted with ether. The organic layer was dried over sodium sulfate and concentrated under reduced pressure to give ethyl 2-(1-(naphthalen-1-yl)-4-(trimethylsilyl)-1H-1,2,3-triazol-5-ylthio)acetate as a yellow oil, that was used in the next step without further purification (1 g, 89%).

Provenance & Evidence