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

HRID 1038579Notes

Reaction equation

HRID 1038579 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

Conditions

Temperature
120 °C

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, bromoacetaldehyde diethyl acetal (1.76 mL, 11.7 mmol) was added at 0° C., and the mixture was stirred at 120° C. overnight. The reaction solution was added water at room temperature, and extracted with diethylether. The organic layer was washed with brine, dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by silica-gel column chromatography (hexane). The title compound (2.69 g (yield >100%)) was obtained as a yellow oil.

Workup

  1. additionwas added at 0° C.
  2. extractionextracted with diethylether
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by silica-gel column chromatography (hexane)

Sources & evidence

ORD record
ord-1e257593c92645959f353bc43a403cd2
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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