Azobisisobutyronitrile → 2,6-Dichloro-3-nitrobenzyl Bromide

HRID 1872495Notes

Reaction equation

HRID 1872495 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([Cl:11])[C:3]=1[CH3:12].CC(N=NC(C#N)(C)C)(C#N)C.C1C(=O)N([Br:32])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:32][CH2:12][C:3]1[C:4]([Cl:11])=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimide2×HCID 971552,6-Dichloro-3-nitrotoluene

Product 1

HCID 110115352,6-Dichloro-3-nitrobenzyl Bromide

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 1,3-dichloro-2-methyl-4-nitro-benzene (19) (6.18 g, 30 mmol) and AIBN (200 mg) in CCl4 (75 mL), NBS (7.96 g, 45 mmol) was added under stirring and reflux. The reaction was monitored by 1H-NMR (CDCl3). Additional NBS (5×7.96 g, total of 270 mmol) was added till the starting material was consumed. The reaction mixture was filtered hot, and the filtrate was evaporated to dryness. The crude was column chromatographed (SiO2, hexanes:EtOAc, 9:1 to 8.5:1.5). The product was obtained as a low melting white solid: yield 6.869 g, 80%. 1H-NMR (CDCl3) δ 4.75 (s, 2H), 7.45, d, 1H, J=8.5 Hz), 7.69 (d, 1H, J=8.5 Hz); MS (CI) m/z 285 (M+H). Anal Calcd for C7H4BrCl2NO2 : C, 29.51; H, 1.42; N, 4.92. Found: C, 29.09; H, 1.43; N, 4.71.

Workup

  1. temperaturereflux
  2. customwas consumed
  3. filtrationThe reaction mixture was filtered hot
  4. customthe filtrate was evaporated to dryness
  5. customchromatographed (SiO2, hexanes:EtOAc, 9:1 to 8.5:1.5)
  6. customThe product was obtained as

Sources & evidence

ORD record
ord-3a897cae2d8b4c619c5a0832c43959be
Source dataset
uspto-grants-2000_08
Patent number
US06110911

Reaction notes

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