Hydrogen Peroxide → 4-Benzyl-2-iodobenzenamine

HRID 2075244Notes

Reaction equation

HRID 2075244 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:15]I.OO.O>CO>[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]([NH2:14])=[C:12]([I:15])[CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 807IodineHCID 962WaterHCID 136914Benzenamine, 4-(phenylmethyl)-

Product 1

HCID 584153354-Benzyl-2-iodobenzenamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-benzylbenzenamine (3.00 g, 16.4 mmol) in 16 mL MeOH was added iodine (2.49 g, 9.82 mmol) followed by hydrogen peroxide, 30% in water (1.67 mL, 16.4 mmol). The dark solution was allowed to stir overnight. The reaction was partitioned between water/brine and EtOAc. The organic layer was washed 1× brine, dried over MgSO4, filtered, and concentrated. The resulting oil was purified by ISCO (120 g, 0-10% EtOAc/hexanes) to give 4-benzyl-2-iodobenzenamine as a red oil which slowly solidified to a red solid. MS (ESI) m/z: Calculated: 309.0; Observed: 310.0 (M++1).

Workup

  1. customThe reaction was partitioned between water/brine and EtOAc
  2. washThe organic layer was washed 1× brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting oil was purified by ISCO (120 g, 0-10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-2fcd6f8ec0324d83a7df282c3b43d41b
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

Loading…