Allyltributylstannane → 5-Allyl-2,1,3-benzoxadiazole

HRID 1187089ノート

反応式

HRID 1187089 の反応式
Br[C:2]1[CH:10]=[CH:9][C:5]2=[N:6][O:7][N:8]=[C:4]2[CH:3]=1.[Cl-].[Li+].[CH2:13]([Sn](CCCC)(CCCC)CCCC)[CH:14]=[CH2:15]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:15]([C:2]1[CH:10]=[CH:9][C:5]2=[N:6][O:7][N:8]=[C:4]2[CH:3]=1)[CH:14]=[CH2:13]

参加物

6

反応物 3

HCID 90628AllyltributylstannaneHCID 433294Lithium ChlorideHCID 27762985-Bromo-2,1,3-benzoxadiazole

生成物 1

HCID 595687145-Allyl-2,1,3-benzoxadiazole

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

実験手順

5-Bromo-2,1,3-benzoxadiazole (10 g, 50.3 mmol) was dissolved in toluene (300 mL) and treated with lithium chloride (6.39 g, 151 mmol), Pd(Ph3P)4 (2.90 g, 2.51 mmol), and allyltributylstannane (18.66 ml, 60.3 mmol). Degassed and refluxed the mixture under N2 for 3 hrs. The reaction mixture turned black. Poured the reaction mixture into water and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried, and evaporated to dryness. The residue was chromatographed through 120 g ISCO Redi-Sep column and eluted with 0-10% ethyl acetate/hexane to yield 5-(prop-2-en-1-yl)-2,1,3-benzoxadiazole.

後処理

  1. customDegassed
  2. temperaturerefluxed the mixture under N2 for 3 hrs
  3. additionPoured the reaction mixture into water
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with brine
  7. customdried
  8. customevaporated to dryness
  9. customThe residue was chromatographed through 120 g ISCO Redi-Sep column
  10. washeluted with 0-10% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-4bf0cbdd74214d759c662c6e9f2a2b08
出典データセット
uspto-grants-2014_03
特許番号
US08673920B2

反応ノート

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