2-Bromonaphthalene → 2-Bromo-9,10-di-naphthalene-2-yl-9,10-dihydro-anthracene-9,10-diol

HRID 890836

反応式

HRID 890836 の反応式
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[Li][C:13]([CH3:16])([CH3:15])[CH3:14].[Br:17][C:18]1[CH:31]=[CH:30][C:29]2[C:28](=[O:32])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21](=[O:33])[C:20]=2[CH:19]=1>C1COCC1.CCCCC>[Br:17][C:18]1[CH:31]=[CH:30][C:29]2[C:28]([C:2]3[CH:11]=[CH:10][C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH:3]=3)([OH:32])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]([C:5]3[CH:4]=[CH:9][C:16]4[C:13](=[CH:15][CH:3]=[CH:2][CH:11]=4)[CH:14]=3)([OH:33])[C:20]=2[CH:19]=1

参加物

6

反応物 3

HCID 113722-BromonaphthaleneHCID 2210132-BromoanthraquinoneHCID 178418306HCID 178418306、化合物

生成物 1

HCID 222471662-Bromo-9,10-di-naphthalene-2-yl-9,10-dihydro-anthracene-9,10-diol収率 93%

試薬・触媒・溶媒 2

HCID 8003Pentane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-bromonaphthalene (6.49 g, 31.3 mmol) in dry THF (50 ml) was added dropwise t-BuLi (18.4 ml of a 1.7 M solution in pentane) at −78° C. under nitrogen. After the mixture had been stirred for 30 min, 2-bromoanthraquinone (3.00 g, 10.4 mmol) was added at −78° C. The cooling bath was removed and the mixture was stirred for 2 hours at room temperature. The mixture was quenched with saturated aqueous ammonium chloride solution (50 ml) and extracted with ethyl ether (3×50 ml). The combined organic extracts were dried over MgSO4 and concentrated under vacuum. The crude product was slurried in petroleum ether, filtered off with suction, and washed with petroleum ether. After drying, the 2-bromo-9,10-di-naphthalene-2-yl-9,10-dihydro-anthracene-9,10-diol (5.30 g, 93%) was obtained.

後処理

  1. customThe cooling bath was removed
  2. stirringthe mixture was stirred for 2 hours at room temperature
  3. customThe mixture was quenched with saturated aqueous ammonium chloride solution (50 ml)
  4. extractionextracted with ethyl ether (3×50 ml)
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. concentrationconcentrated under vacuum
  7. filtrationfiltered off with suction
  8. washwashed with petroleum ether
  9. customAfter drying

出典と根拠

ORDレコード
ord-03bcbf3dd5ef4e5199d1c034360cbe7f
出典データセット
uspto-grants-2006_02
特許番号
US06998487B2

関連ノート

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