Water → Diethyl [(2-bromophenyl)methyl]phosphonate

HRID 1797285Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1797285
[P:1]([O-:8])([O:5][CH2:6][CH3:7])[O:2][CH2:3][CH3:4].[H-].[Na+].[Br:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14]Br.O>C1COCC1>[Br:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14][P:1](=[O:8])([O:5][CH2:6][CH3:7])[O:2][CH2:3][CH3:4]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 769652-Bromobenzyl bromideHCID 3780918Diethylphosphite

Produkt 1

HCID 12703598Diethyl [(2-bromophenyl)methyl]phosphonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Diethyl phosphite (0.77 mL, 6.0 mmol) was dissolved in dry THF (10 mL) in a dry schlenk tube under an argon atmosphere. The solution was cooled on an ice bath and NaH (0.24 g, 60% in oil, 6.0 mmol) was added and stirred for 5 min. 2-bromo-benzylbromide (1.0 g, 4.0 mmol) dissolved in 2 mL dry THF was added and the reaction mixture was refluxed overnight. H2O (20 mL) was added and the water phase was extracted with EtOAc (3×10 mL). The combined organic phases were washed with brine, dried (MgSO4), filtered and evaporated in vacuo. The crude product was purified by flash chromatography using EtOAc as the eluent to afford the title compound as a colourless oil.

Aufarbeitung

  1. temperatureThe solution was cooled on an ice bath
  2. additionwas added
  3. temperaturethe reaction mixture was refluxed overnight
  4. extractionthe water phase was extracted with EtOAc (3×10 mL)
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b700946425f1468599053d311fe24f72
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07034015B2

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