1,2-Dibromoethane → HCID 68183475、化合物

HRID 513697ノート

反応式

HRID 513697 の反応式
[Mg].BrCCBr.Br[C:7]1[CH:8]=[CH:9][C:10]([F:18])=[C:11]([CH:13]2[O:17][CH2:16][CH2:15][O:14]2)[CH:12]=1.[N+:19]([C:22]1[C:23]([CH:32]=[O:33])=[CH:24][CH:25]=[C:26]2[C:31]=1[N:30]=[CH:29][CH:28]=[CH:27]2)([O-:21])=[O:20]>C1COCC1>[O:14]1[CH2:15][CH2:16][O:17][CH:13]1[C:11]1[CH:12]=[C:7]([CH:32]([C:23]2[C:22]([N+:19]([O-:21])=[O:20])=[C:31]3[C:26]([CH:27]=[CH:28][CH:29]=[N:30]3)=[CH:25][CH:24]=2)[OH:33])[CH:8]=[CH:9][C:10]=1[F:18]

参加物

6

反応物 4

HCID 78391,2-DibromoethaneHCID 5462224MagnesiumHCID 117695548-Nitro-7-quinolinecarboxaldehydeHCID 184555852-(5-Bromo-2-fluorophenyl)-1,3-dioxolane

生成物 1

HCID 68183475HCID 68183475、化合物収率 74%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Magnesium (983 mg, 40.5 mmol) was suspended in anhydrous THF (30 ml). 1,2-dibromoethane (0.17 ml, 2.02 mmol) was added and the solution was stirred at room temperature for 20 min. 2-(5-bromo-2-fluoro-phenyl)-[1,3]dioxolane 417 (3.2 g, 12.95 mmol) was added dropwise and the mixture was heated at 40° C. for 2 h. The mixture was allowed to cool to room temperature. The Grignard reagent (0.43M; 28.6 ml) was added to a suspension of 8-nitroquinoline-7-carbaldehyde 204 (2.5 g, 12.4 mmol) in dry THF (30 ml) at 0° C. under a nitrogen atmosphere. The mixture was stirred at room temperature for 30 min. The mixture was quenched with sat. NH4Cl (10 ml) and the aqueous phase was extracted with EtOAc (20 ml). The organic phase was washed with brine (10 ml), dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with heptane/EtOAc (50:50) as the eluent to give the title compound (3.39 g, 74%).

後処理

  1. temperaturethe mixture was heated at 40° C. for 2 h
  2. temperatureto cool to room temperature
  3. stirringThe mixture was stirred at room temperature for 30 min
  4. customThe mixture was quenched with sat. NH4Cl (10 ml)
  5. extractionthe aqueous phase was extracted with EtOAc (20 ml)
  6. washThe organic phase was washed with brine (10 ml)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified by column chromatography with heptane/EtOAc (50:50) as the eluent

出典と根拠

ORDレコード
ord-6dadb1431f37459f8b87789e4d0ac191
出典データセット
uspto-grants-2015_08
特許番号
US09102688B2

反応ノート

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