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Chemical Structure| 816421-98-4 Chemical Structure| 816421-98-4

Structure of 816421-98-4

Chemical Structure| 816421-98-4

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Product Details of [ 816421-98-4 ]

CAS No. :816421-98-4
Formula : C28H22BNO2
M.W : 415.29
SMILES Code : OB(C1=CC=C(C2=CC=C(N(C3=C4C=CC=CC4=CC=C3)C5=CC=CC=C5)C=C2)C=C1)O

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Application In Synthesis of [ 816421-98-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 816421-98-4 ]

[ 816421-98-4 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 352359-42-3 ]
  • [ 816421-98-4 ]
YieldReaction ConditionsOperation in experiment
Synthesis of 4'-(naphthylphenylamino)triphenylene-4-carbaldehyde (3N); To a three-necked round-bottom flask containing 2N (6.82 g=15.2 mmol) was added dropwise BuLi (16.1 mmol, 1.6 M in a hexane solution of 10 mL) in dry THF at -78 C., and then the solution was brought to 0 C. and stirred by a magnetic bar for 30 minutes. The solution was cooled again to -78 C. and to it was added dropwise tri-isopropyl borate (5.3 mL=19.8 mmol). The reaction solution was warmed up gradually to room temperature and stirred overnight. To the reaction solution was then added excess amount (30 mL) of 10% HCl(aq), while the mixture was stirred for another 1 hour. The reaction was quenched by pouring into distilled water, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous MgSO4, and evaporation of the solvent gave a crude product, which was immediately subjected to the next reaction.The crude product was mixed with 4-bromobenzaldehyde (2.57 g=14.0 mmol), K2CO3(aq) (2.76 g=2 mmol) in 10 mL of H2O, and Pd(PPh3)4 (807 mg=0.69 mmol) in dry toluene/THF (2/1). The mixture was heated to 90 C. for 12 hours. After cooling, the products were extracted by ethyl acetate and the organic layer dried over anhydrous MgSO4. The crude product was dried in vacuo and purifies by a silica gel column eluted with CH2Cl2/hexane (1/1). Yellow solid of compound 3N was obtained in 88% yield (6.35 g=13.4 mmol).The spectroscopic data of 3N were as follows: 1H NMR (CDCl3): δ 10.04 (s, 1H), 7.93-7.95 (m, 3H), 7.88 (d, 1H, J=8.1 Hz), 7.78 (t, 3H, J=6.9 Hz), 7.67 (d, 2H, J=8.6 Hz), 7.64 (d, 2H, J=8.6 Hz), 7.44-7.50 (m, 4H), 7.35-7.38 (m, 2H), 7.24 (d, 1H, J=4.2 Hz), 7.21 (d, 2H, J=7.2 Hz), 7.10 (d, 2H, J=8.6 Hz), 7.07 (d, 2H, J=8.6 Hz) and 6.96 (t, 1H, J=7.2 Hz); 13C NMR (CDCl3): δ 191.7, 148.2, 148.0, 146.6, 143.3, 140.8, 137.6, 135.3, 135.1, 132.8, 131.3, 130.3, 129.2, 128.5, 127.7, 127.6, 127.3, 127.0, 126.7, 126.4, 124.5, 124.2, 122.4, 122.3 and 121.5; HRMS (m/z): 475.1933 (M+) (calculated value: 475.1936).
 

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