Benzyl Alcohol → Benzyl 5-Bromoamyl Ether

HRID 344239Notes

Reaction equation

HRID 344239 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]Br.O>CN(C)C=O>[CH2:3]([O:10][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][Br:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 81001,5-DibromopentaneHCID 24758Sodium hydride

Product 1

HCID 14221121Benzyl 5-Bromoamyl EtherYield 100.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

60% Sodium hydride (1.33 g) was suspended in dimethylformamide (40 ml), and benzyl alcohol (3 g) was added under ice-cooilng with stirring. The mixture was stirred at room temperature for 1 hr. The mixture was again ice-cooled, and 1,5-dibromopentane (6.4 g) was added, which was followed by stirring at room temperature for 3 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried and the solvent was evaporated under reduced pressure to give 7.2 g of 5-benzyloxypentyl bromide.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hr
  2. temperaturecooled
  3. stirringby stirring at room temperature for 3 hr
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. customdried
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-787681961d6941eeaafdd570c6fefc2a
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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