Aniline → N-phenyl-2-Dibenzofuranamine

HRID 634544

反応式

HRID 634544 の反応式
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

参加物

7

反応物 3

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

生成物 1

HCID 67204676N-phenyl-2-Dibenzofuranamine収率 65%

試薬・触媒・溶媒 3

HCID 634876Binap, (A+-)-触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d5f29dc01bfa4e10ac9c9be8b6866ec3
出典データセット
uspto-grants-2016_04
特許番号
US09324949B2

関連ノート

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