Boron tribromide → HCID 58012403, compound

HRID 1698584Notes

Reaction equation

HRID 1698584 reaction equation
[Br:1][C:2]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[N:9]([CH3:10])[C:8]2[C:11]([CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:12][CH:13]=[C:14]([O:15]C)[C:7]=2[N:6]=1.B(Br)(Br)Br>ClCCl>[Br:1][C:2]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[N:9]([CH3:10])[C:8]2[C:11]([CH:17]([CH2:18][CH3:19])[CH2:20][CH3:21])=[CH:12][CH:13]=[C:14]([OH:15])[C:7]=2[N:6]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 58012365HCID 58012365, compound

Product 1

HCID 58012403HCID 58012403, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(2-bromo-4-chlorophenoxy)-7-(1-ethylpropyl)-4-methoxy-1-methyl-1H-benzimidazole (80 mg, 0.18 mmol) in dichloromethane (2 mL) was added dropwise a dichloromethane solution (1M, 2 mL) of boron tribromide at 0° C., and stirred at room temperature for 1 h. The reaction mixture was cooled at 0° C., quenched with water, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was washed with isopropyl ether and hexane (1:1) to give the title compound (67 mg, 86%).

Workup

  1. temperatureThe reaction mixture was cooled at 0° C.
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. washThe residue was washed with isopropyl ether and hexane (1:1)

Sources & evidence

ORD record
ord-3ab4e8b21855483e93e58138006c91e6
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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