Quinone → 6,13-Pentacenequinone

HRID 1895564

반응식

HRID 1895564 반응식
Br[CH:2](Br)[C:3]1[C:4]([CH:9](Br)Br)=[CH:5][CH:6]=[CH:7][CH:8]=1.[C:13]1(=[O:20])[CH:18]=[CH:17][C:16](=[O:19])[CH:15]=[CH:14]1.[I-].[Na+]>CN(C=O)C>[CH:5]1[C:4]2[C:3](=[CH:2][C:18]3[C:13](=[O:20])[C:14]4[C:15]([C:16](=[O:19])[C:17]=3[CH:9]=2)=[CH:9][C:4]2[C:3](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:2]=4)[CH:8]=[CH:7][CH:6]=1

참가 물질

5

반응물 3

HCID 4650QuinoneHCID 5238Sodium IodideHCID 832341,2-Bis(dibromomethyl)benzene

생성물 1

HCID 764156,13-Pentacenequinone수율 91%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

To a clear solution of α,α,α′,α′-tetrabromo-o-xylene (30.5 g, 0.073 mol) in DMF (100 mL) was added benzoquinone (3.125 g, 0.03 mol) and sodium iodide (27.25 g, 0.18 mol). The resulting brown suspension was heated and stirred at 120° C. overnight. After cooling to RT, the yellow solids were filtered via vacuum filtration. The yellow solids were washed with water, saturated sodium bisulfite solution and dried to yield the product (8.1 g, 91%). 1H NMR (500 MHz, CDCl3): δ 8.96 (s, 4H), 8.14 (m, 4H), 7.72 (m, 4H). 13C NMR (125.68 MHz, CDCl3): δ 183.2, 135.47, 130.80, 130.30, 129.98, 129.66. m/z: 308 [M+].

후처리

  1. temperatureThe resulting brown suspension was heated
  2. temperatureAfter cooling to RT
  3. filtrationthe yellow solids were filtered via vacuum filtration
  4. washThe yellow solids were washed with water, saturated sodium bisulfite solution
  5. customdried

출처 및 근거

ORD 기록
ord-dd94acd8cb7347b59690211fdb09a179
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513466B2

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