Ethanol → 3-Bromo-5-fluoro-2-iodoaniline

HRID 2379119Notes

Reaction equation

HRID 2379119 reaction equation
[I:1][C:2]1[C:7]([Br:8])=[CH:6][C:5]([F:9])=[CH:4][C:3]=1[N+:10]([O-])=O.O.O.[Sn](Cl)Cl.C(O)C.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[I:1][C:2]1[C:7]([Br:8])=[CH:6][C:5]([F:9])=[CH:4][C:3]=1[NH2:10]

Participants

6

Reactant 4

HCID 702EthanolHCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 194297701-Bromo-5-fluoro-2-iodo-3-nitrobenzene

Product 1

HCID 194297943-Bromo-5-fluoro-2-iodoanilineYield 76%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Treat 1-iodo-2-nitro-4-fluoro-6-bromobenzene (5.0g, 14.46mmol) with tin (II) chloride dihydrate (12g, 58mmol) in refluxing ethanol (150mL). Stir at reflux for 24 hours, pour into a mixture of ethyl acetate (200mL) and saturated sodium hydrogen carbonate (500mL). Filter and wash the filtrate with saturated sodium hydrogen carbonate (200mL) and water (200mL). Dry (MgSO4), evaporate the solvent in vacuo and purify by silica gel chromatography to give the title compound as an off-white solid (3.45g, 76%).

Workup

  1. temperatureat reflux for 24 hours
  2. filtrationFilter
  3. washwash the filtrate with saturated sodium hydrogen carbonate (200mL) and water (200mL)
  4. dry with materialDry (MgSO4)
  5. customevaporate the solvent in vacuo
  6. custompurify by silica gel chromatography

Sources & evidence

ORD record
ord-d8d94aea26dc4d8c98cf90782c95ce4d
Source dataset
uspto-grants-1994_11
Patent number
US05360814

Reaction notes

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