Phosphorus tribromide → 1-[4-(2-Bromoethoxy)phenoxy]-3,5-difluorobenzene

HRID 579955Notes

Reaction equation

HRID 579955 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([F:19])[CH:18]=1)[O:5][C:6]1[CH:15]=[CH:14][C:9]([O:10][CH2:11][CH2:12]O)=[CH:8][CH:7]=1.P(Br)(Br)[Br:21]>CCCCCC>[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([F:19])[CH:18]=1)[O:5][C:6]1[CH:15]=[CH:14][C:9]([O:10][CH2:11][CH2:12][Br:21])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 134559112-[4-(3,5-Difluorophenoxy)phenoxy]ethanol

Product 1

HCID 134559141-[4-(2-Bromoethoxy)phenoxy]-3,5-difluorobenzeneYield 105.7%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a mixture of 2-[4-(3,5-difluorophenoxy)phenoxy]ethanol (1.00 g, 3.76 mmol) and n-hexane (50 ml), phosphorus tribromide (0.71 g, 2.63 mmol) was gradually added with stirring under ice-cooling. After completion of the addition, the temperature was elevated to room temperature and stirring was continued at the same temperature for 30 minutes, followed by stirring under reflux for 1 hour. After allowed to cool, the upper n-hexane layer was collected by decantation, and the n-hexane layer was washed with water two times, an aqueous sodium carbonate solution three times and a saturated aqueous sodium chloride solution once in order and dried over anhydrous magnesium sulfate. Removal of the solvent gave 2-[4-(3,5-difluorophenoxy)phenoxy]ethyl bromide (915 mg).

Workup

  1. additionwas gradually added
  2. temperaturecooling
  3. additionAfter completion of the addition
  4. customwas elevated to room temperature
  5. stirringstirring
  6. stirringby stirring
  7. temperatureunder reflux for 1 hour
  8. temperatureto cool
  9. customthe upper n-hexane layer was collected by decantation
  10. washthe n-hexane layer was washed with water two times
  11. dry with materialan aqueous sodium carbonate solution three times and a saturated aqueous sodium chloride solution once in order and dried over anhydrous magnesium sulfate
  12. customRemoval of the solvent

Sources & evidence

ORD record
ord-fe2120b097014be1a773a3b052b7750b
Source dataset
uspto-grants-1988_06
Patent number
US04751225

Reaction notes

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