Benzyl Bromide → HCID 15446537, compound

HRID 2228177Notes

Reaction equation

HRID 2228177 reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH3:3].[P:6]([O-:13])(OCC)OCC.[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O1C[CH2:25][CH2:24][CH2:23]1>>[CH2:14]([P:6](=[O:13])([CH2:23][CH2:24][CH3:25])[CH2:1][CH2:2][CH3:3])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 4

HCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 3780918DiethylphosphiteHCID 178455851HCID 178455851, compound

Product 1

HCID 15446537HCID 15446537, compound

Procedure

Under nitrogen atmosphere, to a solution of propyl magnesium bromide in tetrahydrofuran (2M, 250 g) was added diethyl phosphite (18.0 g) under ice-cooling, and the mixture was stirred at room temperature for 3 hours. To the reaction mixture was added benzyl bromide (24. 7 ml), and the mixture was refluxed for 5 hours. The reaction mixture was vigorously stirred and added to concentrated hydrochloric acid-ice to stop the reaction. The mixture was extracted with ethyl acetate and concentrated. The residue was separated and purified with column chromatography (ethyl acetate→ethyl acetate/ethanol=3:1) to give benzyldipropylphosphine oxide (25.33 g) as colorless crystals.

Workup

  1. temperaturecooling
  2. temperaturethe mixture was refluxed for 5 hours
  3. stirringThe reaction mixture was vigorously stirred
  4. customthe reaction
  5. extractionThe mixture was extracted with ethyl acetate
  6. concentrationconcentrated
  7. customThe residue was separated
  8. custompurified with column chromatography (ethyl acetate→ethyl acetate/ethanol=3:1)

Sources & evidence

ORD record
ord-050287d03e0e4afca6bf9dbe8b8e36d4
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

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