Dimethylformamide → 4,4'-Bis(3-formylcarbazol-9-yl)biphenyl

HRID 643191

反応式

HRID 643191 の反応式
P(Cl)(Cl)(Cl)=O.CN(C)[CH:8]=[O:9].[CH:11]1[C:23]2[N:22]([C:24]3[CH:29]=[CH:28][C:27]([C:30]4[CH:35]=[CH:34][C:33]([N:36]5[C:48]6[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=6[C:42]6[C:37]5=[CH:38][CH:39]=[CH:40][CH:41]=6)=[CH:32][CH:31]=4)=[CH:26][CH:25]=3)[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]=2[CH:14]=[CH:13][CH:12]=1.[CH2:49]([OH:51])C.ClCCl>O>[CH:49]([C:13]1[CH:12]=[CH:11][C:23]2[N:22]([C:24]3[CH:29]=[CH:28][C:27]([C:30]4[CH:31]=[CH:32][C:33]([N:36]5[C:48]6[CH:47]=[CH:46][C:45]([CH:8]=[O:9])=[CH:44][C:43]=6[C:42]6[C:37]5=[CH:38][CH:39]=[CH:40][CH:41]=6)=[CH:34][CH:35]=4)=[CH:26][CH:25]=3)[C:21]3[C:16]([C:15]=2[CH:14]=1)=[CH:17][CH:18]=[CH:19][CH:20]=3)=[O:51]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 112487164,4'-Bis(9H-carbazol-9-yl)biphenylHCID 21584144Dichloromethane ethanol

生成物 1

HCID 426406674,4'-Bis(3-formylcarbazol-9-yl)biphenyl収率 87%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Phosphorus oxychloride (13 ml, 21.5 g, 140 mmol) was added dropwise to a stirring mixture of N,N-dimethylformamide (5.40 ml, 5.10 g, 69.7 mmol) and 4,4′-bis(carbazol-9-yl)biphenyl (7.72 g, 16.0 mmol) and the resulting mixture was stirred at room temperature for 5 minutes then heated to 90° C. for 24 h. (nb reaction mixture was followed by TLC using 5% ethanol/dichloromethane as the eluent). The reaction mixture was poured into water (800 ml) and this beaker was placed in the ultrasonic bath for 2 hours to break up the material. The mixture was stirred for a further 2 hours then filtered. The residue was washed with water and then hexane and dried in vacuo for 2 hours. The crude product was heated with acetone (3×400 ml) and filtered. The product was insoluble in most organic solvent. The impurities were removed by washing with acetone. The product, 4,4′-bis(3-formyl-carbazol-9-yl)biphenyl, (7.92 g, 87%) was obtained with melting point 295° C. (dec.). Found: C, 81.74; H, 4.71; and N, 4.45. C38H28N2O2.(CH3)2CO requires C, 82.25; H, 5.05; N, 4.68%. 1H n.m.r. (300 MHz, Me2SO): δ 10.09 (2 H, s, CHO); 8.88 (2 H, d, J 0.88 Hz, aromatic H); 8.41 (2 H, d, J 7.61 Hz, aromatic H); 8.41 (4 H, d, J 8.49 Hz, aromatic H); 8.00 (2 H, dd, J 8.49, 1.46 Hz, aromatic H); 7.83 (4 H, d, J 8.49 Hz, aromatic H); 7.38-7.61 (8 H, m, aromatic H). λmax(CH2Cl2): 215 nm (ε/Lmol−1cm−1 9163), 241 (68 488), 272 (65 928), 294 (67 194) 328 (42 620). FT-IR (solid): 3045, 2825, 2730, 1682, 1623, 1591, 1505, 1456, 1438, 1365, 1319, 1275, 1230, 1180, 802, 745 cm−1.

後処理

  1. temperaturethen heated to 90° C. for 24 h. (
  2. customnb reaction mixture
  3. waitthis beaker was placed in the ultrasonic bath for 2 hours
  4. stirringThe mixture was stirred for a further 2 hours
  5. filtrationthen filtered
  6. washThe residue was washed with water
  7. dry with materialhexane and dried in vacuo for 2 hours
  8. temperatureThe crude product was heated with acetone (3×400 ml)
  9. filtrationfiltered
  10. customThe impurities were removed
  11. washby washing with acetone

出典と根拠

ORDレコード
ord-7da25b1bf4ee44b9b1340bced2071a44
出典データセット
uspto-grants-2010_04
特許番号
US07700148B2

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