Iodine → 4-Bromo-2-fluoro-6-iodoaniline

HRID 1512854Notes

Reaction equation

HRID 1512854 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([F:9])[CH:3]=1.[I:10]I>C(O)C.CCOC(C)=O.S([O-])([O-])(=O)=O.[Ag+2]>[Br:1][C:2]1[CH:7]=[C:6]([I:10])[C:5]([NH2:8])=[C:4]([F:9])[CH:3]=1

Participants

6

Reactant 2

HCID 807IodineHCID 1230504-Bromo-2-fluoroaniline

Product 1

HCID 591460824-Bromo-2-fluoro-6-iodoanilineYield 86.2%

Reagents, catalysts & solvents 3

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

(4-bromo-2-fluorophenyl)amine (6 g) was dissolved in ethanol (200 mL), silver sulfate (10.8 g) was added and then iodine (8.8 g) was added in small portions. After the addition was complete, the reaction mixture was stirred at ambient temperature overnight. The reaction mixture was filtered and evaporated to leave a dark oil which was taken up in EtOAc, washed with saturated sodium thiosulphate (100 mL×2), sodium carbonate solution (100 mL×2) and water. The organic layer dried over anhydrous Na2SO4 and evaporated. The crude product was purified by column chromatography to give (4-bromo-2-fluoro-6-iodophenyl)amine (D159) (8.6 g) as a yellow solid. MS (ES): C6H4BrFIN requires 315; found 315.9 (M+H+).

Workup

  1. additionAfter the addition
  2. filtrationThe reaction mixture was filtered
  3. customevaporated
  4. customto leave a dark oil which
  5. washwashed with saturated sodium thiosulphate (100 mL×2), sodium carbonate solution (100 mL×2) and water
  6. dry with materialThe organic layer dried over anhydrous Na2SO4
  7. customevaporated
  8. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-c7b4d4d8c7214f77a32c37db5b319f52
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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