Benzimidazole → HCID 59375036, compound

HRID 661868Notes

Reaction equation

HRID 661868 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8]Br)[C:3]=1[CH3:10].[NH:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[CH:12]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.CCOC(C)=O>[Br:1][C:2]1[C:3]([CH3:10])=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH2:8][N:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[CH:12]1

Participants

6

Reactant 3

HCID 5798BenzimidazoleHCID 11430Potassium CarbonateHCID 226726481-Bromo-3-(bromomethyl)-2-methylbenzene

Product 1

HCID 59375036HCID 59375036, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-bromo-3-(bromomethyl)-2-methylbenzene (250 mg, 0.947 mmol), 1H-benzo[d]imidazole (336 mg, 2.84 mmol) and potassium carbonate (131 mg, 0.947 mmol) in acetonitrile (5 mL) was stirred at rt for 5 h, The mixture was diluted with EtOAc and filtered, and the solid was washed with EtOAc. The filtrate was washed with water, dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from 60:40 hexane-EtOAc to EtOAc), to provide 1-(3-bromo-2-methylbenzyl)-1H-benzo[d]imidazole as a white solid (233 mg, 82%). 1H NMR (400 MHz, chloroform-d) δ 8.14 (1H, s), 7.68-7.78 (1H, m), 7.56 (1H, d, J=7.9 Hz), 7.36-7.44 (1H, m), 7.25-7.34 (2H, m), 7.03 (1H, t, J=7.8 Hz), 6.82 (1H, d, J=7.7 Hz), 5.58 (2H, s), 2.45 (3H, s). Mass spectrum m/z 301, 303 (M+H)+.

Workup

  1. filtrationfiltered
  2. washthe solid was washed with EtOAc
  3. washThe filtrate was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (
  7. washeluting with a gradient from 60:40 hexane-EtOAc to EtOAc),

Sources & evidence

ORD record
ord-77e6773f6bfe4097877a5213ce1d2875
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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