Phenyl-1-naphthylamine → N-(4'-bromo-[1,1'-biphenyl]-4-yl)-N-phenylnaphthalen-1-amine

HRID 1928667

反応式

HRID 1928667 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:15]1([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[Br:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([N:25]([C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=[CH:17][CH:16]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:3][CH:4]=2)=[CH:9][CH:10]=1

参加物

7

反応物 3

HCID 7013Phenyl-1-naphthylamineHCID 71104,4'-DibromobiphenylHCID 23676156Sodium t-butoxide

生成物 1

HCID 16755312N-(4'-bromo-[1,1'-biphenyl]-4-yl)-N-phenylnaphthalen-1-amine収率 70%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

A mixture of 4,4′-dibromobiphenyl (8.46 g=27.4 mmol), Pd(OAc)2 (105 mg=0.18 mmol), dppf (253 mg=0.46 mmol), N-(1-naphthyl)aniline (2.0 g=9.13 mmol) and sodium t-butoxide (1.32 g=13.7 mmol) in dry toluene was placed in a three-necked flask under a nitrogen atmosphere and stirred at 90° C. for 15 h. After cooling, the reaction was quenched by adding water and then extracted by ethyl acetate. The organic layer was dried over anhydrous MgSO4 and evaporated under vacuum. The products were purified by a silica gel column eluted with hexane. White solid of compound 2N was obtained in 70% yield (2.86 g=6.37 mmol).

後処理

  1. customwas placed in a three-necked flask under a nitrogen atmosphere
  2. temperatureAfter cooling
  3. customthe reaction was quenched
  4. additionby adding water
  5. extractionextracted by ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous MgSO4
  7. customevaporated under vacuum
  8. customThe products were purified by a silica gel column
  9. washeluted with hexane

出典と根拠

ORDレコード
ord-445ad050c76a4e5ca7eae9f41f26deb5
出典データセット
uspto-grants-2012_05
特許番号
US08183393B2

関連ノート

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