3-Bromobenzyl bromide → HCID 86729349, compound

HRID 1852431Notes

Reaction equation

HRID 1852431 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-4c8ae5a2d547428cb75bba9088d714f1
Source dataset
uspto-grants-2015_02
Patent number
US08962608B2

Reaction notes

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