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[ CAS No. 397322-46-2 ] {[proInfo.proName]}

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Chemical Structure| 397322-46-2
Chemical Structure| 397322-46-2
Structure of 397322-46-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 397322-46-2 ]

CAS No. :397322-46-2 MDL No. :MFCD23701524
Formula : C10H8BrN Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 222.08 Pubchem ID :-
Synonyms :

Safety of [ 397322-46-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 397322-46-2 ]

* 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.

  • Upstream synthesis route of [ 397322-46-2 ]
  • Downstream synthetic route of [ 397322-46-2 ]

[ 397322-46-2 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 397322-46-2 ]
  • [ 34241-39-9 ]
  • [ 20357-21-5 ]
YieldReaction ConditionsOperation in experiment
26% With N-Bromosuccinimide; NaH In tetrahydrofuran; tetrachloromethane; water; toluene (28-6)
To a solution of the compound of Example 28-5 (194 mg) in carbon tetrachloride (5.0 mL) were added N-bromosuccinimide (156 mg) and 2,2'-azobis(isobutyronitrile) (16.3 mg) under nitrogen atmosphere, and the mixture was heated under reflux for 2 hours.
The reaction solution was cooled to room temperature, and the insoluble materials were removed by filtration.
The solvent was evaporated under reduced pressure to about 3 ml.
Further, toluene was added thereto, and the mixture was evaporated under reduced pressure to about 3 mL.
This procedure was repeated five times to give a solution of a crude bromo compound in toluene.
Under nitrogen atmosphere, a solution of the compound of Reference Example 1 (158 mg) in THF (5.0 mL) was cooled to 0°C, and thereto was added 60 percent NaH (37.06 mg).
Further, thereto was added the solution of the crude bromo compound in toluene, and the mixture was stirred at 50°C for 2 hours.
The reaction solution was cooled to room temperature, and water was added to the mixture, and further extracted twice with ethyl acetate.
The extract was washed with water and a saturated brine, dried over magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure.
The residue was purified by silica gel column (hexane / ethyl acetate =3/ 1 --> 1/1) to give the title compound (90.9 mg, 26 percent).
1H NMR (CDCl3, 400MHz) δ 8.79 (d, 1H, J=2.1Hz), 8.20 (d, 1H, J=2.1Hz), 8.04 (d, 1H, J=8.4Hz), 7.80 (d, 1H, J=7.5Hz), 7.70 (d, 2H, J=8.0Hz), 7.53 (dd, 1H, J=7.5, 8.4Hz), 7.23 (d, 2H, J=8.0Hz), 7.11 (dd, 1H, J=1.7, 2.5Hz), 6.86 (dd, 1H, J=1.7, 4.0Hz), 6.31 (dd, 1H, J=2.5, 4.0Hz), 5.91 (s, 2H), 2.41 (s, 3H).
Reference: [1] Patent: EP1479384, 2004, A1,
  • 2
  • [ 397322-46-2 ]
  • [ 397321-54-9 ]
  • [ 34241-39-9 ]
  • [ 20357-21-5 ]
YieldReaction ConditionsOperation in experiment
26% With N-Bromosuccinimide; NaH In tetrahydrofuran; tetrachloromethane; water; toluene (28-6)
To a solution of the compound of Example 28-5 (194 mg) in carbon tetrachloride (5.0 mL) were added N-bromosuccinimide (156 mg) and 2,2'-azobis(isobutyronitrile) (16.3 mg) under nitrogen atmosphere, and the mixture was heated under reflux for 2 hours.
The reaction solution was cooled to room temperature, and the insoluble materials were removed by filtration.
The solvent was evaporated under reduced pressure to about 3 ml.
Further, toluene was added thereto, and the mixture was evaporated under reduced pressure to about 3 mL.
This procedure was repeated five times to give a solution of a crude bromo compound in toluene.
Under nitrogen atmosphere, a solution of the compound of Reference Example 1 (158 mg) in THF (5.0 mL) was cooled to 0° C., and thereto was added 60percent NaH (37.06 mg).
Further, thereto was added the solution of the crude bromo compound in toluene, and the mixture was stirred at 50° C. for 2 hours.
The reaction solution was cooled to room temperature, and water was added to the mixture, and further extracted twice with ethyl acetate.
The extract was washed with water and a saturated brine, dried over magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure.
The residue was purified by silica gel column (hexane/ethyl acetate=3/1-->1/1) to give the title compound (90.9 mg, 26percent).
1H NMR (CDCl3, 400 MHz) δ 8.79 (d, 1H, J=2.1 Hz), 8.20 (d, 1H, J=2.1 Hz), 8.04 (d, 1H, J=8.4 Hz), 7.80 (d, 1H, J=7.5 Hz), 7.70 (d, 2H, J=8.0 Hz), 7.53 (dd, 1H, J=7.5, 8.4 Hz), 7.23 (d, 2H, J=8.0 Hz), 7.11 (dd, 1H, J=1.7, 2.5 Hz), 6.86 (dd, 1H, J=1.7, 4.0 Hz), 6.31 (dd, 1H, J=2.5, 4.0 Hz), 5.91 (s, 2H), 2.41 (s, 3H).
Reference: [1] Patent: US2003/181496, 2003, A1,
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