1-(2-Bromoethoxy)-4-(trifluoromethoxy)benzene → N-methyl-N-[2-(4-trifluoromethoxyphenoxy)ethyl]amine

HRID 856087Notes

Reaction equation

HRID 856087 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]([F:15])([F:14])[F:13])=[CH:7][CH:6]=1.CO.[CH3:18][NH2:19]>CO>[CH3:18][NH:19][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]([F:15])([F:14])[F:13])=[CH:7][CH:6]=1

Participants

4

Procedure

1-(2-Bromoethoxy)-4-(trifluoromethoxy)benzene (2.2 g, 7.72 mmol) was dissolved in methanol (20 ml), to which 40% methylamine methanol solution (20 ml) was added, and the mixture was heated under reflux for 5 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in methylene chloride, and the mixture was washed with saturated sodium hydrogencarbonate aqueous solution. The organic layer was dried over magnesium sulfate, and filtered, and the filtrate was concentrated under reduced pressure to afford N-methyl-N-[2-(4-trifluoromethoxyphenoxy)ethyl]amine (1.44 g, yield 79%) as a pale yellow oil.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 5 hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. dissolutionthe residue was dissolved in methylene chloride
  6. washthe mixture was washed with saturated sodium hydrogencarbonate aqueous solution
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-de99762eb7d546cca28e5d2f0ceb19f8
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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