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

HRID 18181

반응식

HRID 18181 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

HCID 593449293-Benzyl-7-bromo-5-methyl-benzofuran수율 52.7%

시약·촉매·용매 3

HCID 70681Tetrabutylammonium Chloride촉매HCID 6093782Bis(acetonitrile)dichloropalladium촉매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7ac7c6a36b2d43f6bce03c300bbc3b33
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741326B2

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