Stannous chloride dihydrate → 4-(2-Fluorophenoxy)aniline

HRID 1865092Notes

Reaction equation

HRID 1865092 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][CH:6]=1.O.O.[Sn](Cl)Cl>C(O)C.C(OCC)(=O)C>[F:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([NH2:11])=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 579749991-Fluoro-2-(4-nitrophenoxy)benzene

Product 1

HCID 51260734-(2-Fluorophenoxy)anilineYield 63%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add together 4-(2-fluoro-phenoxy)-nitrobenzene (3.18 g, 13.6 mmol) and Tin(II) chloride dihydrate (12.89 g, 5 Eq.) in absolute ethanol (20 mL) and heat to reflux while stirring under a nitrogen atmosphere for 3 hours. Cool to room temperature and dilute with ethyl acetate (50 mL). Wash this organic layer once with water, dry over potassium carbonate, filter, and concentrate under reduced vacuum to give 2.90 g as a dark oil. Purify the material by silica gel chromatography (Prep. 2000) eluting with methylene chloride to provide 1.74 g of the title compound as a tan solid. Mass spectrum (m/e): 204.2 (M*+1): (Bruker 300) 1H NMR (CDCl3) δ 7.08-7.15 (2H, m), 6.95-7.02 (3H, m), 6.81-6.92 (4H, m), 6.63-6.67 (2H, d).

Workup

  1. temperatureheat
  2. temperatureto reflux
  3. washWash this organic layer once with water
  4. dry with materialdry over potassium carbonate
  5. filtrationfilter
  6. concentrationconcentrate under reduced vacuum
  7. customto give 2.90 g as a dark oil
  8. customPurify the material by silica gel chromatography (Prep. 2000)
  9. washeluting with methylene chloride

Sources & evidence

ORD record
ord-95020244fb9e40eaa5be8c391dd4fa00
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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