9-溴蒽 → 2-bromo-13,13-dimethyl-6,11-di(phenanthren-9-yl)-11,13-dihydro-6H-indeno[1,2-b]anthracene-6,11-diol

HRID 40407笔记

反应方程式

HRID 40407 反应方程式
Br[C:2]1[C:3]2[C:8]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[CH:15]=1)=[CH:7][CH:6]=[CH:5][CH:4]=2.[Li][CH2:17][CH2:18][CH2:19][CH3:20].[Br:21][C:22]1[CH:23]=[C:24]2[C:42](=[CH:43][CH:44]=1)[C:27]1=[CH:28][C:29]3[C:30](=[O:41])[C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][C:36]=4[C:37](=[O:40])[C:38]=3[CH:39]=[C:26]1[C:25]2([CH3:46])[CH3:45]>C1COCC1>[Br:21][C:22]1[CH:23]=[C:24]2[C:42](=[CH:43][CH:44]=1)[C:27]1=[CH:28][C:29]3[C:30]([C:18]4[C:19]5[C:20]([C:2]6[CH:15]=[CH:14][CH:9]=[CH:8][C:3]=6[CH:17]=4)=[CH:7][CH:6]=[CH:5][CH:4]=5)([OH:41])[C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][C:36]=4[C:37]([C:2]4[C:3]5[C:8]([C:9]6[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=6[CH:15]=4)=[CH:7][CH:6]=[CH:5][CH:4]=5)([OH:40])[C:38]=3[CH:39]=[C:26]1[C:25]2([CH3:46])[CH3:45]

参与物

5

反应物 3

HCID 113099-溴蒽HCID 581753611196107-73-9HCID 178418339正丁基锂

产物 1

HCID 873808702-bromo-13,13-dimethyl-6,11-di(phenanthren-9-yl)-11,13-dihydro-6H-indeno[1,2-b]anthracene-6,11-diol收率 72%

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂

实验过程

9-bromophenanthrene (13.88 g, 0.054 mol) was placed in a flask, and THF (200 ml) was added thereto. After dissolution, n-BuLi (38.4 ml, 0.06 mol) was gradually added at −780, and the reaction mixture was stirred for one hour at a maintained temperature. Then, 2-bromo-13,13-dimethyl-6H-indeno[1,2-b]anthracene-6,11(13H)-dione (10 g, 0.024 mol) was added and the reaction mixture was stirred at room temperature for 12 hours. After the reaction was terminated, the reaction solution was washed with distilled water, extracted with ethyl acetate, and purified by column chromatography to give, 2-bromo-13,13-dimethyl-6,11-di(phenanthren-9-yl)-11,13-dihydro-6H-indeno[1,2-b]anthracene-6,11-diol (13.1 g, yield=72%).

后处理

  1. additionwas gradually added at −780
  2. stirringthe reaction mixture was stirred at room temperature for 12 hours
  3. customAfter the reaction was terminated
  4. washthe reaction solution was washed with distilled water
  5. extractionextracted with ethyl acetate
  6. custompurified by column chromatography
  7. customto give

来源与证据

ORD记录
ord-0479e1595a5c4f09821c7eed8bc394c9
来源数据集
uspto-grants-2013_09
专利号
US08525158B2

反应笔记

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