3-Bromobenzyl bromide → HCID 86729349, compound

HRID 521181Notes

Reaction equation

HRID 521181 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.CC(C)([O-])C.[K+].[Br:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23]Br)[CH:18]=1>C1COCC1>[Br:16][C:17]1[CH:18]=[C:19]([CH:20]=[CH:21][CH:22]=1)[CH2:23][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

5

Reactant 3

HCID 699793-Bromobenzyl bromideHCID 23665647Potassium tert-butoxideHCID 178418385HCID 178418385, compound

Product 1

HCID 86729349HCID 86729349, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1H-benzotriazole (0.52 g, 4.4 mmol) in THF (25 mL) was added potassium tert-butoxide (4.6 mL, 4.6 mmol, 1M in THF) followed by the addition of 1-bromo-3-(bromomethyl)benzene (1.0 g, 4.0 mmol). The solution was allowed to stir for 4 hours before the reaction was quenched with saturated aqueous NaHCO3 and diluted with EtOAc. The organic layer was separated and washed with brine, dried over anhydrous MgSO4, filtered, and concentrated to dryness in vacuo. The residue was purified by MPLC on silica gel (using a gradient elution of 0-80% EtOAc/hexanes) to afford the title compound as a white solid.

Workup

  1. customwas quenched with saturated aqueous NaHCO3
  2. additiondiluted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness in vacuo
  8. customThe residue was purified by MPLC on silica gel (
  9. washa gradient elution of 0-80% EtOAc/hexanes)

Sources & evidence

ORD record
ord-cf35a725ed8443a09e4e5c7d473d39dc
Source dataset
uspto-grants-2016_05
Patent number
US09328099B2

Reaction notes

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