Ethyl Bromide → 1-Bromo-4-ethoxy-2,3-difluorobenzene

HRID 516274Notes

Reaction equation

HRID 516274 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[C:3]=1[F:10].Br[CH2:12][CH3:13].[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CCCCCCC>[CH2:12]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([F:10])[C:4]=1[F:9])[CH3:13]

Participants

6

Reactant 3

HCID 6332Ethyl BromideHCID 14798Sodium HydroxideHCID 102199424-Bromo-2,3-difluorophenol

Product 1

HCID 269854911-Bromo-4-ethoxy-2,3-difluorobenzeneYield 97%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalyst2×HCID 8900HeptaneSolvent

Procedure

To an aqueous (400 ml) solution of 4-bromo-2,3-difluorophenol (T-1) (195.0 g), bromoethane (196.2 g) and tetrabutylammonium bromide (hereinafter, abbreviated as TBAB) (24.2 g), sodium hydroxide (75.9 g) was added, and heating agitation was carried out at 80° C. for 6 hours in a nitrogen atmosphere. After completion of the reaction, extraction was carried out with heptane, an organic layer was washed with water and a saturated aqueous solution of sodium chloride, and then the resultant solution was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and thus a black oily matter was obtained. The resultant material was purified by distillation, and thus 1-ethoxy-2,3-difluorobromobenzene (T-2) was obtained as a colorless oily matter (230.0 g, yield: 97%).

Workup

  1. additionwas added
  2. temperatureheating agitation
  3. customAfter completion of the reaction, extraction
  4. washan organic layer was washed with water
  5. dry with materiala saturated aqueous solution of sodium chloride, and then the resultant solution was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthus a black oily matter was obtained
  8. distillationThe resultant material was purified by distillation

Sources & evidence

ORD record
ord-10beaa35c9db43128a1b3ce462c1f165
Source dataset
uspto-grants-2015_08
Patent number
US09109157B2

Reaction notes

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