Aniline → N-phenyl-2-Dibenzofuranamine

HRID 634544

반응식

HRID 634544 반응식
Br[C:2]1[C:7]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:16]1([NH:15][C:12]2[CH:13]=[CH:14][C:9]3[O:8][C:7]4[CH:2]=[CH:3][CH:4]=[CH:5][C:6]=4[C:10]=3[CH:11]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

7

반응물 3

HCID 6115AnilineHCID 4582564-Bromodibenzo[b,d]furanHCID 23676156Sodium t-butoxide

생성물 1

HCID 67204676N-phenyl-2-Dibenzofuranamine수율 65%

시약·촉매·용매 3

HCID 634876Binap, (A+-)-촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

실험 절차

4-bromodibenzo[b,d]furan (3.0 g, 12.1 mmol) and aniline (1.69 g, 18.1 mmol) were mixed in 100 mL of toluene. The solution was bubbled with nitrogen for 15 min. Pd2(dba)3 (0.05 g, 0.05 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.15 g, 0.24 mmol) and sodium t-butoxide (1.7 g, 17.4 mmol) were added. The mixture was refluxed overnight under nitrogen. After cooling, the reaction mixture was filtered through celite/silica pad and the filtrate was concentrated under vacuum. The residue was then purified by column chromatography using DCM:hexane (1:1, v/v) as the eluent. 2.0 g (65%) of a white solid was obtained as the product.

후처리

  1. customThe solution was bubbled with nitrogen for 15 min
  2. temperatureThe mixture was refluxed overnight under nitrogen
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered through celite/silica pad
  5. concentrationthe filtrate was concentrated under vacuum
  6. customThe residue was then purified by column chromatography

출처 및 근거

ORD 기록
ord-d5f29dc01bfa4e10ac9c9be8b6866ec3
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09324949B2

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