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

HRID 1797285ノート

反応式

HRID 1797285 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b700946425f1468599053d311fe24f72
出典データセット
uspto-grants-2006_04
特許番号
US07034015B2

反応ノート

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