Iodine → 3-Iodo-5-nitro-2'-trifluoromethyl-biphenyl-4-ylamine

HRID 1518126Notes

Reaction equation

HRID 1518126 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([F:20])([F:19])[F:18])[CH:7]=[CH:8][C:9]=1[NH2:10])([O-:3])=[O:2].[I:21]I>S([O-])([O-])(=O)=O.[Ag+2].CCO>[I:21][C:8]1[CH:7]=[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([F:18])([F:19])[F:20])[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[C:9]=1[NH2:10]

Participants

5

Reactant 2

HCID 807IodineHCID 509940363-Nitro-2'-trifluoromethyl-biphenyl-4-ylamine

Product 1

HCID 509942803-Iodo-5-nitro-2'-trifluoromethyl-biphenyl-4-ylamineYield 83.1%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolvent

Procedure

The method of Koradin, C. et al. (Tetrahedron 2003, 59, 1571-1587) was used. 3-Nitro-2′-trifluoromethyl-biphenyl-4-ylamine (752 mg, 2.66 mmol, as prepared in Example 6, step A) was placed in a 40 mL vial equipped with a magnetic stir bar, and anhydrous EtOH (27 mL) was added. Iodine (1.4 eq., 945 mg, 3.72 mmol) was added as a solid to the stirred solution. Silver sulfate (1.4 eq., 1.16 g, 3.72 mmol) was added in one portion as a solid, and the reaction was stirred at RT for 24 h. The reaction was filtered, and the solvent was removed under reduced pressure. The residue was dissolved in DCM (30 mL), washed with 10% aq Na2S2O3 (10 mL), dried over anhydrous MgSO4, filtered, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography using a 40-g SiO2 pre-packed column eluting with EtOAc/hexanes, 0:1 to 1:4, v/v, yielding 902 mg (83%) of the title compound. 1H-NMR (400 MHz, CDCl3) δ: 8.17 (d, J=2.0 Hz, 1H), 7.94 (d, J=2.0 Hz, 1H), 7.76 (d, J=7.3 Hz, 1H), 7.58 (t, J=7.6 Hz, 1H), 7.50 (t, J=7.7 Hz, 1H), 7.32 (d, J=7.6 Hz, 1H), 6.74 (br. s., 2H).

Workup

  1. customvial equipped with a magnetic stir bar
  2. filtrationThe reaction was filtered
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in DCM (30 mL)
  5. washwashed with 10% aq Na2S2O3 (10 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure
  9. customThe crude product was purified by column chromatography
  10. washeluting with EtOAc/hexanes, 0:1 to 1:4, v/v

Sources & evidence

ORD record
ord-efa55eaaca8e40f484310efd413223c6
Source dataset
uspto-grants-2012_07
Patent number
US08232409B2

Reaction notes

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