Sodium Nitrite → 3-Hydroxy-5-(pentafluorosulfanyl)benzoic acid

HRID 1258514Notes

Reaction equation

HRID 1258514 reaction equation
N[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:11]([F:16])([F:15])([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([OH:7])=[O:6].N([O-])=[O:18].[Na+]>S(=O)(=O)(O)O.O>[OH:18][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:11]([F:16])([F:15])([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 580857063-Amino-5-pentafluorosulfanylbenzoic acid

Product 1

HCID 581367943-Hydroxy-5-(pentafluorosulfanyl)benzoic acidYield 67.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
-5 °C

Procedure

3-Amino-5-pentafluorosulfanylbenzoic acid (1.5 g, example 2a)) was dissolved in 35% sulfuric acid (45 ml) and cooled to −5° C., and a solution of sodium nitrite (387 mg) in water (40 ml) was added dropwise within 10 min. After 40 min, the cooling bath was removed and the mixture was heated to 100° C. After 4 h, the mixture was cooled and the solution was decanted. The clear acidic solution was extracted five times with ethyl acetate. The combined extracts were dried over magnesium sulfate, filtered and concentrated. The crude product was crystallized from ethyl acetate/heptane. 1 g of the desired compound was obtained.

Workup

  1. customthe cooling bath was removed
  2. temperaturethe mixture was heated to 100° C
  3. waitAfter 4 h
  4. temperaturethe mixture was cooled
  5. customthe solution was decanted
  6. extractionThe clear acidic solution was extracted five times with ethyl acetate
  7. dry with materialThe combined extracts were dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was crystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-eeb8be03532c43218fe4e5900839a33a
Source dataset
uspto-grants-2013_06
Patent number
US08466169B2

Reaction notes

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