Benzyl Bromide → HCID 15446537, compound

HRID 1277162Notes

Reaction equation

HRID 1277162 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-298d9e881f5a4a3ca127e1a79c6e4fae
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

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