2,3,4,5,6-Pentafluorobenzamide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of pentafluorobenzamide (5.00 g, 23.69 mmol) in toluene (60 mL) was added Lawesson's reagent (5.70 g, 14.20 mmol) and the flask fitted with a drying tube. The reaction was refluxed overnight, cooled to room temperature, and isooctane (200 mL) was added causing a precipitate to form. The suspension was filtered (gravity) and the filtrate concentrated yielding an orange oil which solidified. Flash chromatography of this oil (1:1 hexane:methylene chloride with 2% acetic acid) yielded crude pentafluorothiobenzamide as a white solid (mp 92°-93° C.) which was used without any further purification. the flask fitted with a drying tube The reaction was refluxed overnight to form The suspension was filtered (gravity) the filtrate concentrated yielding an orange oil which