Sulfuric Acid → 3,5-Dibromoquinoline

HRID 1364301ノート

反応式

HRID 1364301 の反応式
OS(O)(=O)=O.[Br:6][C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2.C1C(=O)N([Br:24])C(=O)C1>C(Cl)Cl>[Br:6][C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[C:14]([Br:24])[CH:13]=[CH:12][CH:11]=2

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 214133-BromoquinolineHCID 67184N-bromobutanimide

生成物 1

HCID 136597573,5-Dibromoquinoline収率 58%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To concentrated H2SO4 (130 mL) was added dropwise at 0° C., over 80 min, 3-bromoquinoline (50 g) at a rate allowing the internal temperature to be maintained between 0° and 10° C. After the addition was complete, NBS (48 g) was added portionwise and the reaction mixture was stirred at rt overnight. The reaction mixture was poured onto ice (2 L) and the resulting solid was dissolved in DCM (600 mL). The aq. layer was further extracted with DCM (600 mL) and the combined extracts were washed with 1M NaOH (300 mL) and concentrated in vacuo. The residue was adsorbed on SiO2 and the resulting dispersal was loaded on the top of a column and eluted with a DCM-Hex (1-1, 3 L), then DCM (3 L) and finally DCM-ether (1-1, 2 L). The title compound was recovered from the last fraction after evaporation to yield 40 g of a white solid.

後処理

  1. temperatureto be maintained between 0° and 10° C
  2. additionAfter the addition
  3. additionThe reaction mixture was poured onto ice (2 L)
  4. extractionThe aq. layer was further extracted with DCM (600 mL)
  5. washthe combined extracts were washed with 1M NaOH (300 mL)
  6. concentrationconcentrated in vacuo
  7. washeluted with a DCM-Hex (1-1, 3 L)
  8. customThe title compound was recovered from the last fraction
  9. customafter evaporation

出典と根拠

ORDレコード
ord-6c9744a643dc4f3babc239a4e85e85e1
出典データセット
uspto-grants-2011_02
特許番号
US07888359B2

反応ノート

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