Potassium Carbonate → 2,4-Diphenylaniline

HRID 75073

反応式

HRID 75073 の反応式
Br[C:2]1[CH:8]=[C:7](Br)[CH:6]=[CH:5][C:3]=1[NH2:4].[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:10]1([C:2]2[CH:8]=[C:7]([C:2]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:3]=3)[CH:6]=[CH:5][C:3]=2[NH2:4])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 120042,4-DibromoanilineHCID 66827Phenylboronic Acid

生成物 1

HCID 123166382,4-Diphenylaniline収率 163.1%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 1140Toluene溶媒2 回

反応条件

温度
100 °C

実験手順

2,4-dibromoaniline (10 mmol), benzeneboronic acid (24 mmol), tetrakis(triphenylphosphine)palladium(0) (1 mmol) and potassium carbonate (12 g) are put in a two-neck round-bottom flask and dissolved in toluene (30 mL) and H2O (10 mL). Subsequently, the resulting solution is stirred in a bath under a temperature of about 100° C. for 24 hours. After completion of the reaction, toluene is removed. The reaction mixture is extracted with dichloromethane and water, and then being distilled under reduced pressure. The resulting residence is filtered by silica gel column and distilled under reduced pressure again. Next, by re-crystallizing and filtering with dichloromethane and petroleum ether, 2,4-diphenylaniline (2.0 g) is yielded.

後処理

  1. customis removed
  2. extractionThe reaction mixture is extracted with dichloromethane and water
  3. distillationbeing distilled under reduced pressure
  4. filtrationThe resulting residence is filtered by silica gel column
  5. distillationdistilled under reduced pressure again
  6. customNext, by re-crystallizing
  7. filtrationfiltering with dichloromethane and petroleum ether

出典と根拠

ORDレコード
ord-8b5da7c99c7443219ca237e017646c49
出典データセット
uspto-grants-2014_09
特許番号
US08835020B2

関連ノート

読み込み中…