1-Bromo-3-methylbutane → 1-Bromo-4-[(3-methylbutoxy)methyl]benzene

HRID 70565

Reaction equation

HRID 70565 reaction equation
[H-].[Na+].Br[CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7].[Br:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][OH:15])=[CH:12][CH:11]=1.[Cl-].[NH4+]>CN(C)C=O>[Br:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][O:15][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 78911-Bromo-3-methylbutaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 701194-Bromobenzyl alcohol

Product 1

HCID 584522841-Bromo-4-[(3-methylbutoxy)methyl]benzeneYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (purity: 55%, 700 mg) and 1-bromo-3-methylbutane (2.56 mL) were added to a solution of 4-bromobenzylalcohol (2.0 g) in N,N-dimethylformamide (40 mL) under ice-cooling, and the mixture was stirred at room temperature for five hours. A saturated ammonium chloride solution was added to the reaction solution, followed by extraction with a mixture of hexane-ethyl acetate (1:1). The organic layer was dried over sodium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:1→50:1→30:1) to give the title compound (2.31 g, 85%).

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with a mixture of hexane-ethyl acetate (1:1)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was then evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:1→50:1→30:1)

Sources & evidence

ORD record
ord-0119a32b104e4da9b9562b6b942d0ba1
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Linked notes

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