Ethyl Bromide → 1-Ethoxy-2,3-Difluorobenzene

HRID 2068450Notes

Reaction equation

HRID 2068450 reaction equation
[OH-].[Na+].[F:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:5]=1[OH:11].Br[CH2:13][CH3:14]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:13]([O:11][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]([F:10])[C:4]=1[F:3])[CH3:14]

Participants

6

Reactant 3

HCID 6332Ethyl BromideHCID 14798Sodium HydroxideHCID 808792,3-Difluorophenol

Product 1

HCID 27829281-Ethoxy-2,3-DifluorobenzeneYield 97%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Sodium hydroxide (75.9 g) was added to a water (400 ml) solution of 2,3-difluorophenol (T-1) (195.0 g), bromoethane (196.2 g) and tetrabutylammonium bromide (TBAB) (24.2 g), and the mixture was heated with stirring at 80° C. for 6 hours under an atmosphere of nitrogen. After the completion of the reaction, the reaction mixture was extracted with heptane, and the organic layer was washed with water and brine, and then dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure to leave a black oil. The oil was purified by distillation to give 1-ethoxy-2,3-difluorobenzene (T-1) as a colorless oil (230.0 g) in 97% yield.

Workup

  1. temperaturethe mixture was heated
  2. customAfter the completion of the reaction
  3. extractionthe reaction mixture was extracted with heptane
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe solution was concentrated under reduced pressure
  7. customto leave a black oil
  8. distillationThe oil was purified by distillation

Sources & evidence

ORD record
ord-c53dc2e827f5404f821c50a04706cf64
Source dataset
uspto-grants-2012_10
Patent number
US08298632B2

Reaction notes

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