(E)-1-(4-bromo-2-nitrostyryl)pyrrolidine → 4-Bromo-2-nitrobenzaldehyde

HRID 37982

반응식

HRID 37982 반응식
I([O-])(=O)(=O)=[O:2].[Na+].[Br:7][C:8]1[CH:20]=[CH:19][C:11](/[CH:12]=C/N2CCCC2)=[C:10]([N+:21]([O-:23])=[O:22])[CH:9]=1>C1COCC1.O>[Br:7][C:8]1[CH:20]=[CH:19][C:11]([CH:12]=[O:2])=[C:10]([N+:21]([O-:23])=[O:22])[CH:9]=1

참가 물질

4

반응물 2

HCID 10913500(E)-1-(4-bromo-2-nitrostyryl)pyrrolidineHCID 23667635Sodium periodate

생성물 1

HCID 6080994-Bromo-2-nitrobenzaldehyde수율 86%

시약·촉매·용매 1

HCID 21881883Oxolane--water (1/1)용매

실험 절차

To a solution of sodium periodate (298 g, 1.40 mol) in THF—H2O (4 L, 1:1) at 0° C. was added (E)-1-(4-bromo-2-nitrostyryl)pyrrolidine (138 g, 464 mmol). The mixture was stirred for 15 h and then filtered to remove solid precipitates. The aqueous layer from the filtrate was separated and extracted with EtOAc (4×200 mL). The combined organic layers were washed with H2O (2×200 mL), dried over MgSO4, filtered, and concentrated under reduced pressure to give the crude product that was purified by silica gel flash column chromatography (5% EtOAc in hexanes) to afford 91 g (86%) of 4-bromo-2-nitrobenzaldehyde.

후처리

  1. filtrationfiltered
  2. customto remove solid
  3. customprecipitates
  4. customThe aqueous layer from the filtrate was separated
  5. extractionextracted with EtOAc (4×200 mL)
  6. washThe combined organic layers were washed with H2O (2×200 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto give the crude product that
  11. customwas purified by silica gel flash column chromatography (5% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-7c58f615c7d14710be3b75f9a1001369
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524702B2

연결된 노트

불러오는 중…