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

HRID 1797285노트

반응식

HRID 1797285 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b700946425f1468599053d311fe24f72
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07034015B2

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