1,10-Phenanthroline → 4-Bromotriphenylamine

HRID 32282ノート

反応式

HRID 32282 の反応式
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.I[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH-].[K+].N1[C:31]2[C:22](=[CH:23][CH:24]=[C:25]3[C:30]=2N=CC=C3)C=CC=1>>[C:10]1([N:6]([C:5]2[CH:7]=[CH:8][C:2]([Br:1])=[CH:3][CH:4]=2)[C:22]2[CH:31]=[CH:30][CH:25]=[CH:24][CH:23]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

5

反応物 4

HCID 13181,10-PhenanthrolineHCID 78074-BromoanilineHCID 11575IodobenzeneHCID 14797Potassium Hydroxide

生成物 1

HCID 6428384-Bromotriphenylamine収率 161.9%

反応条件

温度
180 °C

実験手順

To a 500 ml flask, 17.2 g (0.1 mol) of 4-bromoaniline, 50 g (0.24 mol) of iodobenzene, 32 g (0.8 mol) of potassium hydroxide, 0.04 g (0.04 mol, 0.4 eq.) of cuprous chloride and 0.08 g (0.04 mol, 0.4 eq.) of phenanthroline were introduced and stirred for 12 hours at 180° C. under nitrogen atmosphere. The reaction mixture was cooled to room temperature and the insoluble solid salt was filtered off. The filtrate was extracted with toluene and distilled water two times and then the organic layer was collected. Toluene was removed from the organic layer under reduced pressure to provide an organic compound. The organic compound was purified by column chromatography using n-hexane as an eluent. Then, the product was precipitated with a small amount of ethanol to provide 21 g of diphenylamino 4-bromobenzene (yield 65%). m/z 324 (M+).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe insoluble solid salt was filtered off
  3. extractionThe filtrate was extracted with toluene
  4. distillationdistilled water two times
  5. customthe organic layer was collected
  6. customToluene was removed from the organic layer under reduced pressure
  7. customto provide an organic compound
  8. customThe organic compound was purified by column chromatography
  9. customThen, the product was precipitated with a small amount of ethanol

出典と根拠

ORDレコード
ord-ef0ebcef42c64db3bcdafd8fa346b2a8
出典データセット
uspto-grants-2008_09
特許番号
US07427445B2

反応ノート

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