Nitric Acid → 3-Nitro-5-pentafluorosulfanylbenzoic Acid

HRID 658010Notes

Reaction equation

HRID 658010 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

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 27792093-(Pentafluorosulfanyl)benzoic acid

Product 1

HCID 596421523-Nitro-5-pentafluorosulfanylbenzoic Acid

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.

Workup

  1. stirringthe mixture was stirred at 75° C
  2. stirringAfter stirring at 75° C. for 8 h
  3. waitthe mixture was left
  4. temperaturethe mixture was heated to 75° C.
  5. stirringwhile stirring for 8 h
  6. waitAfter being left
  7. waitto stand overnight
  8. stirringstirred for 2 h
  9. filtrationThen the precipitate was filtered off with suction
  10. customdried under high vacuum

Sources & evidence

ORD record
ord-782602d0fbde4a1fba7f53fe59e3ed72
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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