Water → 1-broMo-4-((2-Methoxyethoxy)Methyl)benzene

HRID 1977307Notes

Reaction equation

HRID 1977307 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[CH3:10][O:11][CH2:12][CH2:13][OH:14].[H-].[Na+].O>O1CCCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][O:14][CH2:13][CH2:12][O:11][CH3:10])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 685274-Bromobenzyl bromide

Product 1

HCID 219975651-broMo-4-((2-Methoxyethoxy)Methyl)benzene

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To an ice-cooled solution of 4-bromobenzyl bromide (3.00 g) and 2-methoxyethanol (1.04 ml) in tetrahydrofuran (30 ml) was added sodium hydride (60%) (0.58 g) in a stream of nitrogen. The mixture was stirred at this temperature for 15 minutes and at room temperature for further 4 hours. To the mixture was added water (1 ml) under ice-cooling. The reaction mixture was diluted with ethyl acetate and washed successively with water and saturated sodium chloride solution. The organic layer was dried over magnesium sulfate, filtered and evaporated to give 1-bromo-4-(2-methoxyethoxymethyl)benzene (3.10 g) as a pale yellow oil.

Workup

  1. temperaturecooling
  2. washwashed successively with water and saturated sodium chloride solution
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-7abdfb7a7dbe40d1a12de56b40d78f79
Source dataset
uspto-grants-2001_05
Patent number
US06232290B1

Reaction notes

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