Water → 1-Fluoro-2-(4-iodophenoxy)benzene

HRID 1865093Notes

Reaction equation

HRID 1865093 reaction equation
C(ON=O)CC(C)C.[F:9][C:10]1[CH:23]=[CH:22][CH:21]=[CH:20][C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16](N)=[CH:15][CH:14]=1.[I:24]CI.O>C(#N)C>[F:9][C:10]1[CH:23]=[CH:22][CH:21]=[CH:20][C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([I:24])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6346DiiodomethaneHCID 8053Isoamyl NitriteHCID 51260734-(2-Fluorophenoxy)aniline

Product 1

HCID 579753181-Fluoro-2-(4-iodophenoxy)benzeneYield 91.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
55 °C

Procedure

Add isoamylnitrite (2.45 g, 2.5 Eq.) to 4-(2-fluoro-phenoxy)-phenylamine (1.70 g, 8.37 mmol) and diiodomethane (7.84 g, 3.5 Eq.) in acetonitrile (10 mL) while stirring at 55° C. under a nitrogen atmosphere. Slowly heat mixture to 75° C. and heat at this temperature for 3 hours. Cool to room temperature and pour into water, and extract the desired material into ethyl acetate. Wash this organic layer once with water, dry over potassium carbonate, filter, and concentrate under reduced vacuum to give 2.41 g of an oil. Purify the material by silica gel chromatography (Prep. 2000) eluting with hexane/methylene chloride 9:1 to provide 1.60 g of the title compound as a thin oil. Mass spectrum (m/e): 314.0 (M*): (Bruker 300) 1H NMR (CDCl3) δ 7.55-7.60 (2H, d), 7.02-7.20 (4H, m), 6.69-6.72 (2H, d).

Workup

  1. temperatureSlowly heat mixture to 75° C. and heat at this temperature for 3 hours
  2. temperatureCool to room temperature
  3. extractionextract the desired material into ethyl acetate
  4. washWash this organic layer once with water
  5. dry with materialdry over potassium carbonate
  6. filtrationfilter
  7. concentrationconcentrate under reduced vacuum

Sources & evidence

ORD record
ord-d95faa6f97484b5caa8751cd09b15e67
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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