Water → 1-Bromo-3-(2,2-diethoxyethoxy)benzene

HRID 1690202Notes

Reaction equation

HRID 1690202 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH2:11]([O:13][CH:14]([O:17][CH2:18][CH3:19])[CH2:15]Br)[CH3:12].O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:15][CH:14]([O:17][CH2:18][CH3:19])[O:13][CH2:11][CH3:12])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 115633-BromophenolHCID 24758Sodium hydrideHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 154537651-Bromo-3-(2,2-diethoxyethoxy)benzeneYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-bromophenol (1.68 g, 9.77 mmol) in N,N′-dimethylformamide (32 mL), sodium hydride (purity 50%) (516 mg, 10.7 mmol) was added under ice-cold conditions, and bromoacetaldehyde diethylacetal (1.76 mL, 11.7 mmol) was added at 0° C., and the resultant mixture was stirred at 120° C. overnight. The reaction solution was added with water at room temperature and extracted with diethyl ether. The organic layer was washed with brine, dried over anhydrous sodium sulfate, concentrated in vacuo, and purified using silica-gel column chromatography (hexane). 1-Bromo-3-(2,2-diethoxyethoxy)benzene (2.69 g. yield >100%) was obtained as a yellow oil.

Workup

  1. additionwas added at 0° C.
  2. extractionextracted with diethyl ether
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified

Sources & evidence

ORD record
ord-5485ca5aaad54108b15b3ed703b1b87e
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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