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

HRID 593423

반응식

HRID 593423 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-208699a64650400482dcca443a515697
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242964B2

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