Nitric Acid → 3-Nitro-5-pentafluorosulfanylbenzoic Acid
Reaction equation
[F:1][S:2]([F:15])([F:14])([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7].S(=O)(=O)(O)O.[N+:21]([O-])([OH:23])=[O:22]>>[F:1][S:2]([F:12])([F:13])([F:14])([F:15])[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([N+:21]([O-:23])=[O:22])[CH:11]=1)[C:6]([OH:8])=[O:7]Participants
4
Procedure
3-Pentafluorosulfanylbenzoic acid (15 g) was dissolved in fuming nitric acid (120 ml) and stirred at RT with exclusion of moisture. Then concentrated sulfuric acid (7.5 ml) was added and the mixture was stirred at 75° C. After stirring at 75° C. for 8 h, the mixture was left to stand overnight, then further sulfuric acid (1.5 ml) was added and the mixture was heated to 75° C. while stirring for 8 h. After being left to stand overnight, the mixture was added to ice-water and stirred for 2 h. Then the precipitate was filtered off with suction and dried under high vacuum. 13.7 g of 3-pentafluorosulfanyl-5-nitrobenzoic acid were obtained.