Iodine → 2-Iodo-4-(trifluoromethyl)aniline

HRID 1777541Notes

Reaction equation

HRID 1777541 reaction equation
[I:1]I.[F:3][C:4]([F:13])([F:12])[C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1>C(O)C.S([O-])([O-])(=O)=O.[Ag+2]>[I:1][C:10]1[CH:11]=[C:5]([C:4]([F:12])([F:13])[F:3])[CH:6]=[CH:7][C:8]=1[NH2:9]

Participants

5

Reactant 2

HCID 807IodineHCID 99644-(Trifluoromethyl)aniline

Product 1

HCID 27833222-Iodo-4-(trifluoromethyl)anilineYield 61%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolvent

Procedure

Iodine (1.58 g; 6.21 mmol) was added to a stirred mixture of silver sulphate (1.94 g; 6.21 mmol) and 4-(trifluoromethyl)aniline (0.8 mL; 6.21 mmol) in ethanol (40 mL). The reaction mixture was then stirred at room temperature for 18 hours and filtered over celite. The volatiles were removed under reduced pressure and the residue was partitioned between ethyl acetate and a saturated aqueous solution of sodium thiosulfate. The organic layer was washed with brine, dried and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluent 2 to 40% ethyl acetate in heptane) to afford 1.08 g (61%) of the title compound as a red oil.

Workup

  1. filtrationfiltered over celite
  2. customThe volatiles were removed under reduced pressure
  3. customthe residue was partitioned between ethyl acetate
  4. washThe organic layer was washed with brine
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was purified by flash chromatography on silica gel (eluent 2 to 40% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-77a19f5017794154a0c6dc4b3b2add32
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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