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

反応式

HRID 40407 の反応式
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]

参加物

5

反応物 3

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

生成物 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収率 72%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-0479e1595a5c4f09821c7eed8bc394c9
出典データセット
uspto-grants-2013_09
特許番号
US08525158B2

関連ノート

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