Hydrochloric Acid → 1-Bromo-3-(2,2-dimethoxyethoxy)benzene

HRID 2253686Notes

Reaction equation

HRID 2253686 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.[CH3:11][O:12][CH:13]([O:16][CH3:17])[CH2:14]Br.Cl>CN(C)C=O.O>[CH3:11][O:12][CH:13]([O:16][CH3:17])[CH2:14][O:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([Br:3])[CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 115633-BromophenolHCID 24758Sodium hydrideHCID 816722-Bromo-1,1-dimethoxyethane

Product 1

HCID 151587201-Bromo-3-(2,2-dimethoxyethoxy)benzeneYield 92.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 60% sodium hydride. (60 g) in N,N-dimethylformamide (1.4 l) was added dropwise 3-bromophenol (260 g) under ice-cooling. After stirring for 10 minutes, to the solution was added dropwise bromoacetaldehyde dimethyl acetal (318 g) and the mixture was heated with stirring for 3 hours at 90° C. After cooling, water was added to the resulting solution and acidified with 1 M hydrochloric acid and then extracted with ether (3 l). The organic layer was washed with successive water, saturated aqueous sodium bicarbonate solution and saturated aqueous NaCl solution. After drying over anhydrous sodium sulfate, ether was removed in vacuo and the residue was purified by silica gel column chromatography to give 363.3 g of the objective compound.

Workup

  1. temperaturecooling
  2. temperaturethe mixture was heated
  3. stirringwith stirring for 3 hours at 90° C
  4. temperatureAfter cooling
  5. extractionextracted with ether (3 l)
  6. washThe organic layer was washed with successive water, saturated aqueous sodium bicarbonate solution and saturated aqueous NaCl solution
  7. dry with materialAfter drying over anhydrous sodium sulfate, ether
  8. customwas removed in vacuo
  9. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-acd157f5331f40d2bd819a0b5036bda2
Source dataset
uspto-grants-1993_08
Patent number
US05232936

Reaction notes

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