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

HRID 1662915ノート

反応式

HRID 1662915 の反応式
[C:1]1([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[CH:13]=[C:12](B(O)O)[CH:11]=[CH:10]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20][C:21]1[CH:26]=[CH:25][C:24](I)=[CH:23][CH:22]=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.C(COC)OC>[Br:20][C:21]1[CH:26]=[CH:25][C:24]([C:12]2[CH:11]=[CH:10][C:9]3[C:14](=[CH:15][CH:16]=[C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH:8]=3)[CH:13]=2)=[CH:23][CH:22]=1

参加物

7

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 48%

試薬・触媒・溶媒 2

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

実験手順

Under an argon gas atmosphere, 21.9 g (88.3 mmol) of 6-phenylnaphthalene-2-boronic acid, 25.0 g (88.3 mmol) of 4-bromoiodobenzene, 2.00 g (1.77 mmol) of tetrakis(triphenylphosphine) palladium(0), 400 mL of toluene, 100 mL of dimethoxyethane and 132 mL of 2M sodium carbonate solution were mixed, and stirred for 15 hours while being refluxed. After the reaction in the mixture was over, the mixture experienced filtration, through which aqueous phase thereof was eliminated. After organic phase thereof was cleansed by water and dried with magnesium sulfate, toluene was distilled away under reduced pressure. Residue thereof was refined by silica-gel column chromatography, such that 15.3 g of 2-(4-bromophenyl)-6-phenylnaphthalene was obtained with an yield of 48%.

後処理

  1. temperaturewhile being refluxed
  2. customAfter the reaction in the mixture
  3. filtrationfiltration
  4. dry with materialdried with magnesium sulfate, toluene
  5. distillationwas distilled away under reduced pressure
  6. customwas obtained with an yield of 48%

出典と根拠

ORDレコード
ord-c577d53615314959a110599d4dea6944
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…