Potassium Carbonate → 2-(2-Bromo-4-chlorophenoxy)-7-(1-ethylpropyl)-4-(2-furyl)-1-methyl-1H-benzimidazole

HRID 1698586Notes

Reaction equation

Cl[C:2]1[N:6]([CH3:7])[C:5]2[C:8]([CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:9][CH:10]=[C:11]([C:12]3[O:13][CH:14]=[CH:15][CH:16]=3)[C:4]=2[N:3]=1.[Br:22][C:23]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:24]=1[OH:30].C(=O)([O-])[O-].[K+].[K+]>O>[Br:22][C:23]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:24]=1[O:30][C:2]1[N:6]([CH3:7])[C:5]2[C:8]([CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:9][CH:10]=[C:11]([C:12]3[O:13][CH:14]=[CH:15][CH:16]=3)[C:4]=2[N:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 2-chloro-7-(1-ethylpropyl)-4-(2-furyl)-1-methyl-1H-benzimidazole (42 mg, 0.139 mmol), 2-bromo-4-chlorophenol (87 mg, 0.417 mmol) and potassium carbonate (58 mg, 0.417 mmol) was heated at 120° C. for 18 h under an argon atmosphere. The mixture was diluted with water. The aqueous solution was extracted with ethyl acetate. The extract was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel with a 1-20% ethyl acetate/n-hexane gradient mixture to give 45 mg (0.0950 mmol, 68%) of the title compound) as a colorless crystal.

Workup

extractionThe aqueous solution was extracted with ethyl acetate
washThe extract was washed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography on silica gel with a 1-20% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record: ord-53deccd8db9c438fa210eac94e678925
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163935B2

Reaction notes

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