Nitric Acid → 4-Fluoro-3-nitrophenylacetic acid

HRID 715084Notes

Reaction equation

HRID 715084 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[N+:12]([O-])([OH:14])=[O:13]>OS(O)(=O)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:6][C:7]=1[N+:12]([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 98372-(4-Fluorophenyl)acetic acid

Product 1

HCID 111272614-Fluoro-3-nitrophenylacetic acidYield 90%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Treat a 0° C. solution of 4-fluorophenylacetic acid (3 g, 19.46 mmol) in H2SO4 (20 mL) drop wise with nitric acid (0.913 mL, 20.44 mmol) and stir for 1 h. Pour the mixture onto ice, extract with DCM (2×), wash the combined organics with brine, dry over MgSO4 and concentrate to dryness to afford the title compound (3.48 g, 90%). MS (ESI) m/z: 198.1 (M−H+).

Workup

  1. additionPour the mixture onto ice
  2. extractionextract with DCM (2×)
  3. washwash the combined organics with brine
  4. dry with materialdry over MgSO4
  5. concentrationconcentrate to dryness

Sources & evidence

ORD record
ord-1c6d0b02714b4a3982acc2aff709a252
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

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