1,10-菲罗啉 → 4-溴-4',4''-二甲基三苯胺

HRID 265755笔记

反应方程式

HRID 265755 反应方程式
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

参与物

6

反应物 4

HCID 13181,10-菲罗啉HCID 78074-溴苯胺HCID 122074-碘甲苯HCID 14797氢氧化钾

产物 1

HCID 111427014-溴-4',4''-二甲基三苯胺收率 425.8%

试剂、催化剂与溶剂 1

HCID 7237邻二甲苯溶剂

反应条件

温度
100 °C

实验过程

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).

后处理

  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

来源与证据

ORD记录
ord-db3f0ecb9ad14ebba93f6d6ea2806266
来源数据集
uspto-grants-1997_07
专利号
US05648539

反应笔记

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