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
Procedure
3-Pentafluorosulfanylbenzoic acid (5.0 g) was dissolved in fuming nitric acid (20 ml) and stirred at RT with exclusion of moisture. Then concentrated sulfuric acid (3 ml) was added and the mixture was stirred at 75° C. After stirring at 75° C. for 5 h, further sulfuric acid (1.5 ml) was added and, after stirring at 75° C. for 2 h, left to stand overnight. Then the mixture was added to ice-water and stirred for 2 h. The precipitate formed was filtered off with suction and dried under high vacuum. 4.2 g of 3-pentafluorosulfanyl-5-nitrobenzoic acid were obtained. A further 900 mg were obtained from the mother liquor after extracting three times with methylene chloride, drying the combined methylene chloride phases over magnesium sulfate and concentrating the solvent. The precipitate was used in the next stage without further purification.
Workup
- stirringthe mixture was stirred at 75° C
- stirringAfter stirring at 75° C. for 5 h
- stirringafter stirring at 75° C. for 2 h
- waitleft
- stirringstirred for 2 h
- customThe precipitate formed
- filtrationwas filtered off with suction
- customdried under high vacuum
Sources & evidence
- ORD record
- ord-3f72b2f885eb4acfb3cf51820fe3691c
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08853206B2
Reaction notes
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