Bromobenzene → 9-bromo-13,13-dimethyl-6,11-diphenyl-11,13-dihydro-6H-indeno[1,2-b]anthracene-6,11-diol

HRID 40408

反応式

HRID 40408 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li][CH2:9][CH2:10][CH2:11][CH3:12].[Br:13][C:14]1[CH:27]=[CH:26][C:25]2[C:24](=[O:28])[C:23]3[CH:22]=[C:21]4[C:29]5[C:34]([C:35]([CH3:37])([CH3:36])[C:20]4=[CH:19][C:18]=3[C:17](=[O:38])[C:16]=2[CH:15]=1)=[CH:33][CH:32]=[CH:31][CH:30]=5.[CH2:39]1COC[CH2:40]1>>[Br:13][C:14]1[CH:27]=[CH:26][C:25]2[C:24]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)([OH:28])[C:23]3[CH:22]=[C:21]4[C:29]5[C:34]([C:35]([CH3:36])([CH3:37])[C:20]4=[CH:19][C:18]=3[C:17]([C:9]3[CH:40]=[CH:39][CH:12]=[CH:11][CH:10]=3)([OH:38])[C:16]=2[CH:15]=1)=[CH:33][CH:32]=[CH:31][CH:30]=5

参加物

5

反応物 4

HCID 7961BromobenzeneHCID 8028TetrahydrofuranHCID 581752939-bromo-13,13-dimethyl-6H-indeno[1,2-b]anthracene-6,11(13H)-dioneHCID 178418339Butyllithium

生成物 1

HCID 673867679-bromo-13,13-dimethyl-6,11-diphenyl-11,13-dihydro-6H-indeno[1,2-b]anthracene-6,11-diol収率 63%

実験手順

Bromobenzene (8.5 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, 9-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 9-bromo-13,13-dimethyl-6,11-diphenyl-11,13-dihydro-6H-indeno[1,2-b]anthracene-6,11-diol (8.5 g, yield=63%).

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

出典と根拠

ORDレコード
ord-14aad029301941c69d94abba4b869465
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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