Nitric Acid → 3-Nitro-5-pentafluorosulfanylbenzoic Acid

HRID 2277768Notes

Reaction equation

HRID 2277768 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][S:6]([F:19])([F:18])([F:17])([F:16])[C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=[O:11]>S(=O)(=O)(O)O>[N+:1]([C:14]1[CH:13]=[C:9]([CH:8]=[C:7]([S:6]([F:19])([F:17])([F:5])([F:18])[F:16])[CH:15]=1)[C:10]([OH:12])=[O:11])([O-:4])=[O:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 27792093-(Pentafluorosulfanyl)benzoic acid

Product 1

HCID 596421523-Nitro-5-pentafluorosulfanylbenzoic Acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Nitric acid (100%; 4.1 mL) was added dropwise over 30 minutes to a stirred solution of 3-(pentafluoro-λ6-sulfanyl)benzoic acid (5.1 g; 20.6 mmol; ABCR GmbH & CO. KG) in sulfuric acid (17.0 mL) at 0° C. The ice bath was removed and the mixture was stirred for 88 hours at room temperature. The batch was cautiously added to ice. The precipitate was separated, washed with water and finally taken up in ethyl acetate. The organic solution was washed with water, filtered using a Whatman filter and concentrated to give the desired product (4.4 g; 15.0 mmol).

Workup

  1. customThe ice bath was removed
  2. additionThe batch was cautiously added to ice
  3. customThe precipitate was separated
  4. washwashed with water
  5. washThe organic solution was washed with water
  6. filtrationfiltered
  7. filtrationfilter
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-dc1caae822b748e199c617f752d3066f
Source dataset
uspto-grants-2015_09
Patent number
US09133171B2

Reaction notes

Loading…