Iodine → HCID 57419476, compound

HRID 1886790Notes

Reaction equation

HRID 1886790 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-f85ade40286844baa8969b5a5b18a42c
Source dataset
uspto-grants-2013_08
Patent number
US08501238B2

Reaction notes

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