Benzyl Bromide → 35085-32-6

HRID 374710Notes

Reaction equation

HRID 374710 reaction equation
[H-].[Na+].[CH2:3]([O:5][P:6]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])([O:8][CH2:9][CH3:10])=[O:7])[CH3:4].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[Cl-].[NH4+]>CN(C=O)C>[CH2:9]([O:8][P:6]([CH:11]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])([O:5][CH2:3][CH3:4])=[O:7])[CH3:10]

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 25517Ammonium Chloride

Product 1

HCID 27008935085-32-6Yield 40.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.1 g of sodium hydride (60% in oil) was suspended in DMF, and 10 g of ethyl diethylphosphonoacetate was dropwise added thereto at -20° C. under argon atmosphere. The mixture was stirred at room temperature for 30 minutes, and then 9.2 g of benzyl bromide was added thereto 50° C. The mixture was stirred at 50° C. overnight. The reaction solution was poured into a saturated ammonium chloride aqueous solution, and extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated sodium chloride aqueous solution, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/acetone=6/1) to obtain 5.7 g of ethyl 2-diethylphosphono-3-phenylpropionate as colorless oily substance.

Workup

  1. customat -20° C.
  2. custom50° C
  3. stirringThe mixture was stirred at 50° C. overnight
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (n-hexane/acetone=6/1)

Sources & evidence

ORD record
ord-8a733de9c8de4f1ca2d5f4e36e571de7
Source dataset
uspto-grants-1996_01
Patent number
US05481036

Reaction notes

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