Benzoyl Peroxide → 1-(Bromomethyl)-4-iodo-2-nitrobenzene

HRID 456315Notes

Reaction equation

HRID 456315 reaction equation
C1C(=O)N([Br:8])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[I:27][C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[C:30]([N+:35]([O-:37])=[O:36])[CH:29]=1>C(Cl)(Cl)(Cl)Cl>[Br:8][CH2:34][C:31]1[CH:32]=[CH:33][C:28]([I:27])=[CH:29][C:30]=1[N+:35]([O-:37])=[O:36]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 1704814-Iodo-2-nitrotoluene

Product 1

HCID 179660241-(Bromomethyl)-4-iodo-2-nitrobenzeneYield 45%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

NBS (5.45 g, 30.62 mmol) and benzoyl peroxide (75% aq, 200 mg, 0.85 mmol) were added to a solution of 4-iodo-2-nitrotoluene (4.63 g, 17.60 mmol) in CCl4 (60 mL). The mixture was heated to reflux overnight, then cooled to room temperature, concentrated in vacuo, and purified by column chromatography to yield 1-bromomethyl-4-iodo-2-nitrobenzene (2.71 g, 45%). 1H NMR (400 MHz, CDCl3): δ 8.35 (d, 1 H, J=1.8 Hz, Ph-H), 7.93 (dd, 1 H, J=1.8 and 8.1 Hz, Ph-H), 7.30 (d, 1 H, J=8.1 Hz, Ph-H), 4.76 (s, 2 H, PhCH2).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated in vacuo
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-258f0248b123411e91294682231ca38b
Source dataset
uspto-grants-2013_07
Patent number
US08497360B2

Reaction notes

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