Potassium Carbonate → 1-Bromo-3-(2-methoxyethoxy)benzene

HRID 2299037Notes

Reaction equation

HRID 2299037 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1.I[CH2:16][CH2:17][O:18][CH3:19].ClCCOC>CN(C)C=O>[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:16][CH2:17][O:18][CH3:19])[CH:9]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 115633-BromophenolHCID 123162-Chloroethyl methyl etherHCID 791361-Iodo-2-methoxyethane

Product 1

HCID 183796081-Bromo-3-(2-methoxyethoxy)benzeneYield 25.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Anhydrous potassium carbonate (4.2 g, 30.4 mmol) was added to a stirred solution of 3-bromophenol (5.0 g, 28.9 mmol) in anhydrous dimethylformamide (100 ml). After 5 minutes, 1-iodo-2-methoxyethane (Annalen, 1967, 710, 59; 5.9 g, 31.8 mmol) was added and the reaction mixture stirred at room temperature for about 16 hours. At this point the mixture was heated at about 50° C. for approximately 72 hours, before 1-chloro-2-methoxyethane (1.8 ml, 19.8 mmol) was added and heating continued for a further 24 hours. The resulting mixture was evaporated under reduced pressure and the residue partitioned between ethyl acetate and water. The layers were separated and the aqueous layer was further extracted with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried (MgSO4) and concentrated to a red oil, which was purified by flash chromatography using hexane:ethyl acetate (3:1) as eluant, to furnish the title compound as a colourless oil (1.7 g, 25%). δ(CDCl3): 3.43 (s,3H), 3.74 (t,2H), 4.10 (t,2H), 6.87 (d,1H), 7.10 (m,3H).

Workup

  1. additionwas added
  2. temperatureheating
  3. waitcontinued for a further 24 hours
  4. customThe resulting mixture was evaporated under reduced pressure
  5. customthe residue partitioned between ethyl acetate and water
  6. customThe layers were separated
  7. extractionthe aqueous layer was further extracted with ethyl acetate
  8. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated to a red oil, which
  11. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-8c1f9eba88934ba0aed5efe79a03ec59
Source dataset
uspto-grants-2002_12
Patent number
US06495568B1

Reaction notes

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