Water → 1-Bromo-2-(propoxymethyl)benzene

HRID 1169474Notes

Reaction equation

HRID 1169474 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[H-].[Na+].Br[CH2:13][CH2:14][CH3:15].O>C1COCC1>[CH2:13]([O:5][CH2:4][C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[Br:1])[CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 728502-Bromobenzyl alcohol

Product 1

HCID 229900231-Bromo-2-(propoxymethyl)benzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a solution of 2-bromobenzyl alcohol (10.0 g) in THF (100 ml) was added at 0° C. sodium hydride (60%, 2.35 g), and the resulting mixture was stirred at room temperature for 2 hours. 1-Bromopropane (5.8 ml) was added to the reaction mixture, which was stirred at 60° C. for 20 hours. The reaction mixture was mixed with water and was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride and was dried with magnesium sulfate. After concentration under reduced pressure, the residue was subjected to separation and purification using column chromatography (ethyl acetate:hexane 1:9) to obtain 2-bromobenzyl propyl ether (7.88 g) as a colorless oily substance.

Workup

  1. stirringwas stirred at 60° C. for 20 hours
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
  4. dry with materialwas dried with magnesium sulfate
  5. concentrationAfter concentration under reduced pressure
  6. customthe residue was subjected to separation and purification

Sources & evidence

ORD record
ord-9c017f2c0c924d51b06146f08378ef2e
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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