Nitric Acid → 2-(3-fluoro-4-nitrophenyl)acetic acid

HRID 2173384Notes

Reaction equation

HRID 2173384 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13]([OH:15])=[O:14])[CH:9]=[CH:10][CH:11]=1.OS(O)(=O)=O>>[F:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13]([OH:15])=[O:14])[CH:9]=[CH:10][C:11]=1[N+:1]([O-:4])=[O:2]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 676173-Fluorophenylacetic acid

Product 1

HCID 27746652-(3-fluoro-4-nitrophenyl)acetic acid

Procedure

To a stirred solution of HNO3 (0.55 mL) was added a mixture of (3-fluorophenyl)acetic acid (2 g, 13 mmol) and H2SO4 (4 mL) at 0° C. dropwise. After 2 hours, the mixture was diluted with ice-water and extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by prep-TLC to give (3-fluoro-4-nitrophenyl)acetic acid. 1H-NMR (400 MHz, MeOD) δ ppm 8.2˜8.24 (m, 1H), 7.26˜7.3 (m, 2H), 4.06 (s, 2H).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by prep-TLC

Sources & evidence

ORD record
ord-c275f3b7a8934f98aa765108892eb66f
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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