Iodine → 1000802-17-4

HRID 885927Notes

Reaction equation

HRID 885927 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([O:9][C:10]([F:13])([F:12])[F:11])[CH:3]=1.[I:14]I>CCO.S([O-])([O-])(=O)=O.[Ag+2]>[Cl:1][C:2]1[CH:3]=[C:4]([O:9][C:10]([F:11])([F:12])[F:13])[C:5]([NH2:6])=[C:7]([I:14])[CH:8]=1

Participants

5

Reactant 2

HCID 807IodineHCID 27815264-chloro-2-(trifluoromethoxy)aniline

Product 1

HCID 671867381000802-17-4Yield 100.9%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolvent2×

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 4-chloro-2-(trifluoromethoxy)aniline (1.0 g, 4.7 mmol) in EtOH (50 mL) at 50° C. was added a slurry of iodine (1.2 g, 9.6 mmol) and silver sulfate (2.6 g, 8.4 mmol) in EtOH (30 mL). The reaction mixture was stirred in darkness at 50° C. for 24 h, then cooled to r.t. and filtered through Celite®. The filtrate was concentrated in vacuo. Purification by column chromatography (SiO2, 0-55% ethyl acetate/hexanes) gave the title compound (1.6 g, quantitative) as a pale brown solid. δH (CDCl3) 7.59 (1H, d, J 1.7 Hz), 7.18 (1H, d, J 1.7 Hz), 4.35 (2H, br. s). LCMS (ES+) 337.8 (M+H)+, RT 3.81 minutes (Method 5).

Workup

  1. temperaturecooled to r.t.
  2. filtrationfiltered through Celite®
  3. concentrationThe filtrate was concentrated in vacuo
  4. customPurification by column chromatography (SiO2, 0-55% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-8d9a8507357247f584e20d0ee4af1fc4
Source dataset
uspto-grants-2012_08
Patent number
US08242116B2

Reaction notes

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