Azobisisobutyronitrile → tert-butyl 2-(bromomethyl)-1H-benzo[d]imidazole-1-carboxylate

HRID 1601095Notes

Reaction equation

HRID 1601095 reaction equation
C1C(=O)N([Br:8])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.[C:21]([N:28]1[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[N:30]=[C:29]1[CH3:37])([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]>C(Cl)(Cl)(Cl)Cl>[C:21]([N:28]1[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[N:30]=[C:29]1[CH2:37][Br:8])([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 11183867tert-butyl2-methyl-1H-benzo[d]imidazole-1-carboxylate

Product 1

HCID 11381356tert-butyl 2-(bromomethyl)-1H-benzo[d]imidazole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

NBS (8.43 g, 47.4 mmole) and AIBN (2.1 g, 12.8 mmole) were added to a solution of 1-BOC-2-methylbenzimidazole (10.0 g, 43.1 mmole) in CCl4 (120 mL) at reflux. After 21 hr, the reaction was cooled and filtered. The filtrate was concentrated, and the resulting brown oil was chromatographed on silica gel (15% EtOAc/hexanes) to afford the title product: 1H NMR (400 MHz, CDCl3) δ 7.94-8.01 (m, 1 H), 7.70-7.75 (m, 1 H), 7.31-7.44 (m, 2 H), 4.96 (s, 2 H), 1.75 (s, 9 H),

Workup

  1. temperatureat reflux
  2. temperaturethe reaction was cooled
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customthe resulting brown oil was chromatographed on silica gel (15% EtOAc/hexanes)

Sources & evidence

ORD record
ord-286272d812cf4264924507aed5b12056
Source dataset
uspto-grants-1999_11
Patent number
US05977101

Reaction notes

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