Iodine → HCID 57419476, compound

HRID 1962324Notes

Reaction equation

HRID 1962324 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:3]=1[NH2:4].C(=O)(O)[O-].[Na+].[I:18]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>O>[Br:1][C:2]1[CH:8]=[C:7]([I:18])[CH:6]=[C:5]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:3]=1[NH2:4]

Participants

6

Reactant 4

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 20351179HCID 20351179, compound

Product 1

HCID 57419476HCID 57419476, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 50 mL round-bottom flask was added 2-bromo-6-tert-butylaniline [prepared by the method of Onitsuka, et. al. Organometallics, 25(5), 2006, pp 1270-1278] (1.18 g, 5.17 mmol) and sodium bicarbonate (0.782 g, 9.31 mmol) in water (5 ml). The mixture was cooled in an ice bath and iodine (1.444 g, 5.69 mmol) was added in several portions. The mixture was warmed to ambient temperature and stirred for 16 h. The mixture was treated with aqueous sodium thiosulfate, extracted by ethyl acetate, dried with sodium sulfate, filtered and evaporated. The residue was purified on silica gel eluting with 5% ethyl acetate in hexane to give an oil (1.2 g, 65%).

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. extractionextracted by ethyl acetate
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified on silica gel eluting with 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-a33be630ae9647e69acf15b547798348
Source dataset
uspto-grants-2013_04
Patent number
US08415351B2

Reaction notes

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