Toluene → 2-(4-Bromophenyl)-6-phenylnaphthalene

HRID 1662917ノート

反応式

HRID 1662917 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[C:9]1([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[CH:21]=[C:20](B(O)O)[CH:19]=[CH:18]3)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.C(COC)OC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:20]2[CH:19]=[CH:18][C:17]3[C:22](=[CH:23][CH:24]=[C:15]([C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)[CH:16]=3)[CH:21]=2)=[CH:4][CH:3]=1

参加物

8

反応物 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 115221-Bromo-4-iodobenzeneHCID 57539613(6-Phenylnaphthalen-2-yl)boronic acid

生成物 1

HCID 575398112-(4-Bromophenyl)-6-phenylnaphthalene収率 73.2%

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
90 °C

実験手順

Under an argon gas atmosphere, 20.0 g (70.7 mmol) of 4-bromoiodobenzene, 17.5 g (70.7 mmol) of 6-phenylnaphthalene-2-boronic acid, 1.63 g (1.41 mmol) of tetrakis(triphenylphosphine) palladium(0), 200 mL of toluene, 50 mL of dimethoxyethane and 107 mL of 2M sodium carbonate solution were mixed, and stirred for 10 hours at 90 degrees C. Subsequently, the reaction mixture was cooled down to room temperature, added with water and stirred for one hour. After the solid precipitated during the reaction was separated by filtration, the obtained solid was cleansed with water, methanol, dimethoxyethane and toluene in this order. By dissolving the obtained solid in toluene and refining the solution by silica-gel column chromatography, 18.6 g of 2-(4-bromophenyl)-6-phenylnaphthalene was obtained at an yield of 73%.

後処理

  1. temperatureSubsequently, the reaction mixture was cooled down to room temperature
  2. stirringstirred for one hour
  3. customAfter the solid precipitated during the reaction
  4. customwas separated by filtration
  5. dissolutionBy dissolving the obtained solid in toluene

出典と根拠

ORDレコード
ord-efe494dd18ed4cdbbef535cdf74e24c7
出典データセット
uspto-grants-2011_10
特許番号
US08034256B2

反応ノート

読み込み中…