Acetic Acid → 5-Bromo-2-fluoroaniline

HRID 606819Notes

Reaction equation

HRID 606819 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([N+:9]([O-])=O)[CH:3]=1.C(O)(=O)C>[Fe].O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([NH2:9])[CH:3]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 27363284-Bromo-1-fluoro-2-nitrobenzene2×

Product 1

HCID 27694075-Bromo-2-fluoroanilineYield 67.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

Add 4-bromo-1-fluoro-2-nitrobenzene (19.4 g, 88.2 mmol) and 10 g of fine mesh iron to a solution of acetic acid (75 mL) and water (5 mL) and heat to 105° C. for 4 h or until the 4-bromo-1-fluoro-2-nitrobenzene is completely consumed. Concentrate to remove most of the acetic acid, pour into water and extract with ethyl acetate. Wash the ethyl acetate layers with water, an aqueous saturated solution of sodium chloride, dry (potassium carbonate), filter and concentrate. Purify the residue by silica gel chromatography, eluting with hexanes:ethyl acetate, to give the title compound as an amber oil (11.3 g, 67%).

Workup

  1. customis completely consumed
  2. concentrationConcentrate
  3. customto remove most of the acetic acid
  4. additionpour into water
  5. extractionextract with ethyl acetate
  6. washWash the ethyl acetate layers with water
  7. dry with materialan aqueous saturated solution of sodium chloride, dry (potassium carbonate)
  8. filtrationfilter
  9. concentrationconcentrate
  10. customPurify the residue by silica gel chromatography
  11. washeluting with hexanes

Sources & evidence

ORD record
ord-18d4c5e538224f1fb3715e34cf492c15
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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