Methyl iodide → 2-(3-bromophenyl)-1-methyl-1H-benzimidazole

HRID 2047400

Reaction equation

HRID 2047400 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[NH:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH3:19]I>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]([CH3:19])[C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2788222-(3-Bromophenyl)benzimidazole

Product 1

HCID 9624512-(3-bromophenyl)-1-methyl-1H-benzimidazoleYield 90.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(3-bromophenyl)-1H-benzimidazole (7.8 g, 28.6 mmol) was completely dissolved in dry THF (300 ml), then NaH 60% m/m (1.49 g, 37.2 mmol) was added portionwise to the clear yellow solution. The light brown suspension was stirred 1 h rt, then CH3I (2.5 ml, 40.0 mmol) was added dropwise. The reaction mixture was stirred rt overnight. The reaction was quenched with H2O (300 ml), and extracted with EtOAc (2×450 ml). The organic extracts were dried over MgSO4, filtered and evaporated, to afford the compound as a brown-yellow solid (7.4 g, 70%).

Workup

  1. stirringThe reaction mixture was stirred rt overnight
  2. customThe reaction was quenched with H2O (300 ml)
  3. extractionextracted with EtOAc (2×450 ml)
  4. dry with materialThe organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-459a304f0b5a471bbd25385bb302f100
Source dataset
uspto-grants-2013_11
Patent number
US08592463B2

Linked notes

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