Toluene → N4,N4,N4'-Triphenyl-[1,1'-biphenyl]-4,4'-diamine

HRID 2091440

反応式

HRID 2091440 の反応式
[C:1]1([N:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:24]1[CH:36]=[CH:35][C:27]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:26][CH:25]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].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(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.O>[C:1]1([N:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:13]=[CH:12][C:11]([C:32]3[CH:33]=[CH:34][C:29]([NH:28][C:27]4[CH:35]=[CH:36][CH:24]=[CH:25][CH:26]=4)=[CH:30][CH:31]=3)=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

8

反応物 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 64257864-BromodiphenylamineHCID 121669344-(Diphenylamino)phenylboronic Acid (contains varying amounts of Anhydride)

生成物 1

HCID 22013295N4,N4,N4'-Triphenyl-[1,1'-biphenyl]-4,4'-diamine収率 81.4%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl触媒HCID 962Water溶媒

実験手順

4-(diphenylamino)phenylboronic acid (4.87 g, 16.8 mmol), 4-bromo-N-phenylaniline (3.5 g, 14 mmol), potassium phosphate (9.2 g, 42 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (0.23 g, 0.56 mmol) were added to a three-neck flask under nitrogen. 200 mL of toluene and 20 mL of water was then added. The solution was degassed with nitrogen for 20 minutes. Pd2(dba)3 (0.13 g, 0.14 mmol) was added to the mixture. The mixture was then heated up to reflux overnight. After cooled to room temperature, the organic layer was separated and dried over magnesium sulfate. After evaporating solvent, the residue was purified by column chromatography using 1:2 dichloromethane and hexanes as eluent. 4.7 g of desired product was obtained. (81% yield)

後処理

  1. customThe solution was degassed with nitrogen for 20 minutes
  2. temperatureThe mixture was then heated up
  3. temperatureto reflux overnight
  4. customthe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. customAfter evaporating solvent
  7. customthe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-e54bba8890714effaf8a5159aeabcd93
出典データセット
uspto-grants-2013_05
特許番号
US08440326B2

関連ノート

読み込み中…