1-Bromo-2-fluorobenzene → 2,4-diphenyl-N-2-fluorophenylbenzenamine

HRID 75074

反応式

HRID 75074 の反応式
[C:1]1([C:7]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:11]=[CH:10][C:8]=2[NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[F:27].[Na]>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]>[C:1]1([C:7]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:11]=[CH:10][C:8]=2[NH:9][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[F:27])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

6

反応物 3

HCID 612591-Bromo-2-fluorobenzeneHCID 5360545SodiumHCID 123166382,4-Diphenylaniline

生成物 1

HCID 593575922,4-diphenyl-N-2-fluorophenylbenzenamine収率 61.9%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒2 回

反応条件

温度
100 °C

実験手順

2,4-diphenylaniline (12 mmol), 1-bromo-2-fluorobenzene (10 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.15 mmol), (±)-2,2′-bis(diphenylphosphine)-1,1′-binaphthalene (0.3 mmol) and sodium tert-butoxie (14 mmol) are put in a two-neck round-bottom flask and dissolved in toluene (30 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-diphenyl-N-2-fluorophenylbenzenamine (2.1 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-bc715d726b214670b8b515c9efd95368
出典データセット
uspto-grants-2014_09
特許番号
US08835020B2

関連ノート

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