Phosphorus tribromide → HCID 70428664, compound

HRID 1262868Notes

Reaction equation

HRID 1262868 reaction equation
P(Br)(Br)[Br:2].[C:5]1(/[C:11](=[CH:14]\[F:15])/[CH2:12]O)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C1(C)C=CC=CC=1>[C:5]1(/[C:11](=[CH:14]\[F:15])/[CH2:12][Br:2])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 69506992HCID 69506992, compound

Product 1

HCID 70428664HCID 70428664, compoundYield 176.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of phosphorous tribromide (227 mg) in toluene (2 ml) is slowly added to a solution of (E)-2-phenyl-3-fluoroallyl alcohol (305 mg) in toluene at about -5° so that the temperature does not rise above 0°. The cooling bath is removed and stirring is continued for 3 hours. The reaction mixture is then poured into saturated, aqueous potassium carbonate (20 ml). The mixture is extracted with ether, and the ether solution is washed with water and dried (MgSO4). Evaporation of solvent gives (E)-2-phenyl-3-fluoroallyl bromide (318 mg); colorless oil;

Workup

  1. customdoes not rise above 0°
  2. customThe cooling bath is removed
  3. additionThe reaction mixture is then poured into saturated, aqueous potassium carbonate (20 ml)
  4. extractionThe mixture is extracted with ether
  5. washthe ether solution is washed with water
  6. dry with materialdried (MgSO4)
  7. customEvaporation of solvent

Sources & evidence

ORD record
ord-d9c1642eee2141388d9b6780540d679b
Source dataset
uspto-grants-1984_06
Patent number
US04454158

Reaction notes

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