Hydrochloric Acid → HCID 15965627, compound

Participants

Reaction Conditions

Reaction Steps

3.09 g of TMEDA were dissolved in 30 ml of THF (anhydrous) and added dropwise at −90° C. to 20.5 ml of a 1.3M solution of sec-butyllithium in cyclohexane. A solution of 3.0 g of 4-pentafluorosulfanylbenzoic acid in 20 ml of THF (anhydrous) was then added dropwise at −90° C. After stirring at −90° C. for one hour, a solution of 5.15 g of methyl iodide in 20 ml of THF (anhydrous) was added dropwise. The temperature was kept at −80° C. during this. After stirring at −78° C. for 20 minutes, 100 ml of water were injected, a dilute aqueous HCl solution was used to adjust to pH=1, and the mixture was extracted 3 times with 100 ml of MTB each time. After drying over MgSO4, the solvent was removed in vacuo. The residue was initially chromatographed on silica gel with DIP/2% HOAc, and 1.60 g of a mixture of 4-pentafluorosulfanylbenzoic acid and 4-pentafluorosulfanyl-2-methylbenzoic acid were obtained. This mixture was rechromatographed under the following conditions:

Provenance & Evidence