Ethanol → 5-Bromo-1-ethoxy-2,3-difluorobenzene

HRID 566846Notes

Reaction equation

HRID 566846 reaction equation
F[C:2]1[CH:3]=[C:4]([Br:10])[CH:5]=[C:6]([F:9])[C:7]=1[F:8].[OH-].[K+].[CH2:13]([OH:15])[CH3:14]>>[F:9][C:6]1[CH:5]=[C:4]([Br:10])[CH:3]=[C:2]([O:15][CH2:13][CH3:14])[C:7]=1[F:8]

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 14797Potassium HydroxideHCID 6114091-Bromo-3,4,5-trifluorobenzene

Product 1

HCID 212636535-Bromo-1-ethoxy-2,3-difluorobenzene

Procedure

To a 500 ml three neck flask provided with a stirrer, thermometer, and cooling tube were added 25.0 g (118.5 mmol) of 3,4,5-trifluorobromobenzene, 19.9 g (355.5 mmol) of potassium hydroxide, and 20 ml of ethanol, and heated to reflux while being stirred for 3 hours. After finishing of the reaction, unreacted ethanol was distilled off under a reduced pressure, 200 ml of water was added thereto, and it was extracted with 200 ml of diethyl ether. The extract was washed with water (150 ml) thrice and dried over anhydrous magnesium sulfate. The colorless oily product in an amount of 27.8 g which was obtained by distilling off the solvent was purified by silica gel column chromatography (eluent: heptane, Rf=0.36) to obtain 23.3 g of colorless oily 3,4-difluoro-5-ethoxybromobenzene.

Workup

  1. temperaturethermometer, and cooling tube
  2. temperatureheated
  3. temperatureto reflux
  4. distillationwas distilled off under a reduced pressure, 200 ml of water
  5. additionwas added
  6. extractionit was extracted with 200 ml of diethyl ether
  7. washThe extract was washed with water (150 ml) thrice
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe colorless oily product in an amount of 27.8 g which was obtained
  10. distillationby distilling off the solvent
  11. customwas purified by silica gel column chromatography (eluent: heptane, Rf=0.36)

Sources & evidence

ORD record
ord-fdfb2f2b954642e4844cc4b6d1576cf7
Source dataset
uspto-grants-2001_01
Patent number
US06177154B1

Reaction notes

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