Phosphorus tribromide → HCID 22759278, compound

HRID 460845Notes

Reaction equation

HRID 460845 reaction equation
P(Br)(Br)[Br:2].[C:5]([O:8][CH:9]([CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[C:10]#[C:11][CH2:12]O)(=[O:7])[CH3:6]>CCOCC>[C:5]([O:8][CH:9]([CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[C:10]#[C:11][CH2:12][Br:2])(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 22759281HCID 22759281, compound

Product 1

HCID 22759278HCID 22759278, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Phosphorus tribromide (10.6 g., 0.039 mole) is added dropwise during 15 minutes to a solution of 4-acetoxy-5-(4-fluorophenoxy)-2-pentyn-1-ol (25.1 g., 0.10 mole) in ether (80 ml.). The resulting solution is stirred at room temperature for 1 hour and then heated at reflux for 30 minutes. The solution is poured into 100 ml. of ice water. The organic layer is separated, washed with water and dried over Na2SO4. The solvent is evaporated under reduced pressure to leave the title compound as a light yellow oil.

Workup

  1. temperatureheated
  2. temperatureat reflux for 30 minutes
  3. additionThe solution is poured into 100 ml
  4. customThe organic layer is separated
  5. washwashed with water
  6. dry with materialdried over Na2SO4
  7. customThe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-9f2a9b2d49534898a3dee23bed80b90a
Source dataset
uspto-grants-1977_12
Patent number
US04061643

Reaction notes

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