Iodine → 4-Bromo-2-iodo-5-(trifluoromethyl)aniline

HRID 513850Notes

Reaction equation

HRID 513850 reaction equation
[I:1]I.[Br:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][C:5]=1[C:11]([F:14])([F:13])[F:12]>S([O-])([O-])(=O)=O.[Ag+2].C(O)C>[Br:3][C:4]1[C:5]([C:11]([F:12])([F:13])[F:14])=[CH:6][C:7]([NH2:8])=[C:9]([I:1])[CH:10]=1

Participants

5

Reactant 2

HCID 807IodineHCID 678524-Bromo-3-(trifluoromethyl)aniline

Product 1

HCID 455880634-Bromo-2-iodo-5-(trifluoromethyl)aniline

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolvent

Procedure

Iodine (1.4 g, 5.5 mmol, 1.1 eq.) was gradually added to a mixture solution of 4-bromo-3-trifluoromethyl aniline (1.2 g, 1.0 mmol), silver sulfate (1.72 g, 5.5 mmol, 1.1 eq.), and anhydrous ethanol (35 ml). This was stirred at room temperature for two and half hours. The reaction mixture was filtered through Celite, and washed with ethyl acetate. The wash solution was washed with aqueous solutions of 10% sodium thiosulfate, saturated sodium bicarbonate, and saturated sodium chloride, and then dried over anhydrous sodium sulfate. The desiccant was removed by filtration, and concentration was performed. Crude solid 4-bromo-2-iodo-5-trifluoromethyl-phenylamine was obtained by concentration under reduced pressure. The resulting crude product was used in subsequent reactions without being purified.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washwashed with ethyl acetate
  3. washThe wash solution was washed with aqueous solutions of 10% sodium thiosulfate, saturated sodium bicarbonate, and saturated sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe desiccant was removed by filtration, and concentration

Sources & evidence

ORD record
ord-a22897a594704894a4d0c627c0fb8bfc
Source dataset
uspto-grants-2015_08
Patent number
US09102692B2

Reaction notes

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