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

HRID 37982

反応式

HRID 37982 の反応式
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

参加物

4

反応物 2

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

生成物 1

HCID 6080994-Bromo-2-nitrobenzaldehyde収率 86%

試薬・触媒・溶媒 1

HCID 21881883Oxolane--water (1/1)溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-7c58f615c7d14710be3b75f9a1001369
出典データセット
uspto-grants-2013_09
特許番号
US08524702B2

関連ノート

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