Sodium Carbonate → 3-Benzyl-7-bromo-5-methyl-benzofuran

HRID 18181

反応式

HRID 18181 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4](I)[C:3]=1[O:10][CH2:11][CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+].C([O-])=O.[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CC#N.CC#N.Cl[Pd]Cl.CN(C=O)C>[CH2:13]([C:12]1[C:4]2[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([Br:1])[C:3]=2[O:10][CH:11]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 2723810Sodium FormateHCID 685856031-Bromo-3-iodo-5-methyl-2-(3-phenylallyloxy)-benzene

生成物 1

HCID 593449293-Benzyl-7-bromo-5-methyl-benzofuran収率 52.7%

試薬・触媒・溶媒 3

HCID 70681Tetrabutylammonium Chloride触媒HCID 6093782Bis(acetonitrile)dichloropalladium触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

1-Bromo-3-iodo-5-methyl-2-(3-phenylallyloxy)-benzene (10.86 g, 25 mmol), tetrabutylammonium chloride (7.65 gm, 27.5 mmol), sodium carbonate (6.62 g, 62.46 mmol), sodium formate (1.7 g, 25 mmol), and bis(acetonitrile)dichloropalladium(II) (0.467 g, 1.8 mmol) was added to 50 ml DMF. The mixture was degassed and heated under nitrogen at 80° C. for 105 minutes, then cooled to room temperature. Water was added and the mixture was extracted with a hexanes/ethyl acetate (1:1) mixture. The solution was dried onto 20 gm silica gel, the silica gel was layered over 100 gm silica gel in a fritted funnel and eluted with four 400 ml portions of hexanes. The hexanes was removed under reduced pressure to give 3-benzyl-7-bromo-5-methyl-benzofuran (3.97 g, 52% yield). MS: (M+H)+ 302.

後処理

  1. customThe mixture was degassed
  2. temperaturecooled to room temperature
  3. additionWater was added
  4. extractionthe mixture was extracted with a hexanes/ethyl acetate (1:1) mixture
  5. customThe solution was dried onto 20 gm silica gel
  6. customthe silica gel was layered over 100 gm silica gel in a fritted funnel
  7. washeluted with four 400 ml portions of hexanes
  8. customThe hexanes was removed under reduced pressure

出典と根拠

ORDレコード
ord-7ac7c6a36b2d43f6bce03c300bbc3b33
出典データセット
uspto-grants-2010_06
特許番号
US07741326B2

関連ノート

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