Water → HCID 21995846, compound

HRID 1978747Notes

Reaction equation

HRID 1978747 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:16]([O:18][CH2:19][CH2:20]Br)[CH3:17].O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:17][CH2:16][O:18][CH2:19][CH3:20])=[C:4]([CH3:9])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 168964-Bromo-2-methylphenolHCID 611412-Bromoethyl ethyl ether2×

Product 1

HCID 21995846HCID 21995846, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-bromo-2-methylphenol (9.3 g) in DMF (50 ml) was added potassium carbonate (9.62 g) and then was added dropwise 2.-bromoethyl ethyl ether (7.99 g), and the mixture was stirred at 70° C. for 3 days. To the mixture was added dropwise 2-bromoethyl ethyl ether (1.52 g), and the mixture was stirred at 70° C. for 4.5 hours and cooled. To the mixture was added water, and the mixture was extracted with ether. The organic layer was washed with 1N sodium hydroxide solution and saturated brine, and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was distilled under reduced pressure (3 mmHg, 170° C.) to give colorless oil of 4-bromo-2-methyl-(2-ethoxyethoxy)benzene (10.6 g).

Workup

  1. additionwas added dropwise 2
  2. temperaturecooled
  3. extractionthe mixture was extracted with ether
  4. washThe organic layer was washed with 1N sodium hydroxide solution and saturated brine
  5. dry with materialdried with magnesium sulfate
  6. customUnder reduced pressure, the solvent was evaporated
  7. distillationthe residue was distilled under reduced pressure (3 mmHg, 170° C.)

Sources & evidence

ORD record
ord-3324e2f627224132a30fad049ee9853b
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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