Iodine → 2-Tert-butyl-4-iodoaniline

HRID 530668Notes

Reaction equation

HRID 530668 reaction equation
[C:1]([C:5]1[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=1[NH2:7])([CH3:4])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+].[I:17]I>O>[C:1]([C:5]1[CH:11]=[C:10]([I:17])[CH:9]=[CH:8][C:6]=1[NH2:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 807IodineHCID 805742-tert-ButylanilineHCID 516892Sodium Bicarbonate

Product 1

HCID 121603822-Tert-butyl-4-iodoaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

In a 500 mL round-bottomed flask was combined 2-tert-butylaniline (7.46 g, 50 mmol) and sodium bicarbonate (7.56 g, 90 mmol) in water (50 mL). The mixture was cooled to 0° C. and iodine (12.69 g, 50.0 mmol) was added portion-wise over 20 minutes. The mixture was stirred for 16 hours at room temperature, partitioned between ethyl acetate and 10% aqueous sodium thiosulfate and stirred vigorously for 20 minutes. The ethyl acetate layer was washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to give a dark oil that was purified on an Isco 120 g silica cartridge eluting with ethyl acetate/hexane (0% to 10%) to give the title compound.

Workup

  1. customIn a 500 mL round-bottomed flask was combined
  2. custompartitioned between ethyl acetate and 10% aqueous sodium thiosulfate
  3. stirringstirred vigorously for 20 minutes
  4. washThe ethyl acetate layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a dark oil that
  9. customwas purified on an Isco 120 g silica cartridge
  10. washeluting with ethyl acetate/hexane (0% to 10%)

Sources & evidence

ORD record
ord-9c6e0469a70b4c67bc268e07e9f6add5
Source dataset
uspto-grants-2016_05
Patent number
US09353091B2

Reaction notes

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