Quinone → 6,13-Pentacenequinone

HRID 1895564

反応式

HRID 1895564 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 764156,13-Pentacenequinone収率 91%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

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+].

後処理

  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

出典と根拠

ORDレコード
ord-dd94acd8cb7347b59690211fdb09a179
出典データセット
uspto-grants-2013_08
特許番号
US08513466B2

関連ノート

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