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

HRID 1610784

반응식

HRID 1610784 반응식
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

참가 물질

6

반응물 3

HCID 113722-BromonaphthaleneHCID 2210132-BromoanthraquinoneHCID 178418306HCID 178418306, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 8003Pentane용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e36c353889f04976be3e3322e335d23f
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06984462B2

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