Hydrogen Peroxide → 2-Iodo-4-octylaniline

HRID 2046132Notes

Reaction equation

HRID 2046132 reaction equation
[CH2:1]([C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].OO.[I:18]I>CO>[I:18][C:14]1[CH:15]=[C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH:10]=[CH:11][C:12]=1[NH2:13]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 807IodineHCID 853464-Octylaniline

Product 1

HCID 121652542-Iodo-4-octylanilineYield 173.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred mixture of 4-octyl aniline (0.33 g, 1.6 mmol) and H2O2 (30%, 0.5 ml) in CH3OH (1.5 ml) was added I2 (0.2 g, 0.8 mmol) and the mixture was stirred overnight at room temperature. The solvent was distilled off and the residue was diluted to 10 ml with CH2Cl2, washed with H2O, dried over MgSO4 and filtered. The filtrate was evaporated to dryness to give the title compound (0.46 g, 86%) as yellow paste. 1H NMR (CDCl3) 7.44 (d, 1H, J=1.83 Hz); 6.93 (dd, 1H, J=8.07, 1.86 Hz); 6.65 (d, 1H, J=8.1 Hz); 4.1 (b, 2H); 2.43 (t, 2H, J=7.5 Hz); 1.54-1.49 (m, 2H); 1.26 (b, 10H); 0.87 (t, 3H, J=6.39 Hz).

Workup

  1. distillationThe solvent was distilled off
  2. additionthe residue was diluted to 10 ml with CH2Cl2
  3. washwashed with H2O
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-c98c3ba786e049019567847bb258c73d
Source dataset
uspto-grants-2013_11
Patent number
US08592399B2

Reaction notes

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