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

HRID 333459Notes

Reaction equation

HRID 333459 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, 1H, J=1.8 Hz, Ph-H), 7.93 (dd, 1H, J=1.8 and 8.1 Hz, Ph-H), 7.30 (d, 1H, J=8.1 Hz, Ph-H), 4.76 (s, 2H, 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-a0eea956b0084883959f77b0b79f0b2a
Source dataset
uspto-grants-2014_11
Patent number
US08877905B2

Reaction notes

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