Iodine chloride → HCID 67185750, compound

HRID 885915Notes

Reaction equation

HRID 885915 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.[I:14]Cl.C([O-])(O)=O.[Na+]>Cl>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[C:9]([F:10])([F:11])[F:12])=[CH:4][C:3]=1[I:14]

Participants

5

Reactant 3

HCID 24640Iodine chlorideHCID 901384-TrifluoroacetylanilineHCID 516892Sodium Bicarbonate

Product 1

HCID 67185750HCID 67185750, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a stirred solution of 1-(4-aminophenyl)-2,2,2-trifluoroethanone (1.0 g, 5.28 mmol) in 1M aqueous HCl solution (70 mL) was added iodine monochloride (0.77 g, 4.76 mmol). The reaction mixture was stirred at r.t. for 2 h, then basified with the addition of aqueous sat. NaHCO3 solution and extracted with EtOAc (2×100 mL). The combined organic fractions were dried (Na2SO4), filtered and concentrated in vacuo. Purification by column chromatography (SiO2, 15-20% EtOAc/hexanes) gave the title compound (0.983 g, 59%) as a cream solid. δH (CDCl3) 8.40 (1H, d, J 1.0 Hz), 7.92-7.85 (1H, m), 6.76 (1H, d, J 8.6 Hz), 4.91 (2H, br. s). LCMS (ES+) RT 2.86 minutes (Method 3).

Workup

  1. extractionextracted with EtOAc (2×100 mL)
  2. dry with materialThe combined organic fractions were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by column chromatography (SiO2, 15-20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7abd715be9434be39ad5aa4f3b25797c
Source dataset
uspto-grants-2012_08
Patent number
US08242116B2

Reaction notes

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