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

HRID 925309Notes

Reaction equation

HRID 925309 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

2-iodo-4-(trifluoromethyl)aniline was prepared according to method D Step I with iodine (1.58 g; 6.21 mmol), silver sulphate (1.94 g; 6.21 mmol) and 4-(trifluoromethyl)aniline (0.8 mL; 6.21 mmol) in ethanol (40 mL). 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 2-iodo-4-(trifluoromethyl)aniline as a red oil.

Workup

  1. custom2-iodo-4-(trifluoromethyl)aniline was prepared
  2. customThe crude residue was purified by flash chromatography on silica gel (eluent 2 to 40% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-a27a73fa55ab414c922eaecbe0119092
Source dataset
uspto-grants-2016_03
Patent number
US09284271B2

Reaction notes

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