1,10-Phenanthroline → 4-Bromo-4',4''-dimethyltriphenylamine

HRID 265755ノート

反応式

HRID 265755 の反応式
I[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[Br:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1.N1[C:30]2[C:21](=[CH:22][CH:23]=[C:24]3[C:29]=2N=CC=C3)[CH:20]=CC=1.[OH-].[K+]>C1(C)C(C)=CC=CC=1>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([N:14]([C:24]2[CH:29]=[CH:30][C:21]([CH3:20])=[CH:22][CH:23]=2)[C:13]2[CH:15]=[CH:16][C:10]([Br:9])=[CH:11][CH:12]=2)=[CH:3][CH:4]=1

参加物

6

反応物 4

HCID 13181,10-PhenanthrolineHCID 78074-BromoanilineHCID 122074-IodotolueneHCID 14797Potassium Hydroxide

生成物 1

HCID 111427014-Bromo-4',4''-dimethyltriphenylamine収率 425.8%

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

反応条件

温度
100 °C

実験手順

In a 500 milliliter three-necked flask equipped with a mechanical stirrer, thermometer and Dean-Stark trap, all under an argon atmosphere, were added molten p-iodotoluene (27.3 grams, 125 millimoles), 22 grams of xylene, p-bromoaniline (8.7 grams, 50 millimoles), and 1,10-phenanthroline (1.8 grams, 10 millimoles). The reaction mixture was then heated to 100° C. at which point potassium hydroxide flake (22.4 grams, 400 millimoles) and cuprous chloride (1 gram, 10 millimoles) were added. The temperature was then adjusted to 125° C., and the reaction progress monitored by high performance liquid chromatography. Analysis showed the reaction to be 94 percent complete at 2 hours and 98 percent complete at 5 hours at which point the reaction was terminated. Product isolation was accomplished by adding 24 grams of acetic acid, and partitioning the reaction mixture between 100 grams of toluene and 100 grams of deionized water. The organic phase was further washed several times with deionized water, and the solvent removed to afford 15 grams (84.5 percent) of the desired product of high purity (HPLC, 98 area percent).

後処理

  1. customIn a 500 milliliter three-necked flask equipped with a mechanical stirrer
  2. additionwere added
  3. customwas then adjusted to 125° C.
  4. customthe reaction
  5. customcomplete at 2 hours
  6. customthe reaction was terminated
  7. additionby adding 24 grams of acetic acid
  8. custompartitioning the reaction mixture between 100 grams of toluene and 100 grams of deionized water
  9. customthe solvent removed

出典と根拠

ORDレコード
ord-db3f0ecb9ad14ebba93f6d6ea2806266
出典データセット
uspto-grants-1997_07
特許番号
US05648539

反応ノート

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