9-Bromophenanthrene → 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

반응식

HRID 40407 반응식
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]

참가 물질

5

반응물 3

HCID 113099-BromophenanthreneHCID 581753612-Bromo-13,13-dimethyl-6H-indeno(1,2-b)anthracene-6,11(13H)-dioneHCID 178418339Butyllithium

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-0479e1595a5c4f09821c7eed8bc394c9
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08525158B2

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