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

HRID 1078429

Reaction equation

HRID 1078429 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 (5.0 g, 14.46 mmol) with tin (II) chloride dihydrate (12 g, 58 mmol) in refluxing ethanol (150 mL). Stir at reflux for 24 hours, pour into a mixture of ethyl acetate (200 mL) and saturated sodium hydrogen carbonate (500 mL). Filter and wash the filtrate with saturated sodium hydrogen carbonate (200 mL) and water (200 mL). Dry (MgSO4), evaporate the solvent in vacuo and purify by silica gel chromatography to give the title compound as an off-white solid (3.45 g, 76%).

Workup

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

Sources & evidence

ORD record
ord-612d69fd98c442d1b8b9c0e0315fa898
Source dataset
uspto-grants-1996_08
Patent number
US05547991

Linked notes

Loading…