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Chemical Structure| 1532-97-4 Chemical Structure| 1532-97-4
Chemical Structure| 1532-97-4

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Product Details of 4-Bromoisoquinoline

CAS No. :1532-97-4
Formula : C9H6BrN
M.W : 208.05
SMILES Code : C2=CC1=C(C(=CN=C1)Br)C=C2
MDL No. :MFCD00006904
InChI Key :SCRBSGZBTHKAHU-UHFFFAOYSA-N
Pubchem ID :73743

Safety of 4-Bromoisoquinoline

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 4-Bromoisoquinoline

* 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 [ 1532-97-4 ]
  • Downstream synthetic route of [ 1532-97-4 ]

[ 1532-97-4 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 1532-97-4 ]
  • [ 394-67-2 ]
YieldReaction ConditionsOperation in experiment
60%
Stage #1: With n-butyllithium In tetrahydrofuran at -65℃; for 0.5 h;
Stage #2: With N-fluorobis(benzenesulfon)imide In tetrahydrofuran at -65℃; for 2 h;
To a solution of n-butyl lithium (133 mL, 332.5 mmol, 2.5 M in THF) in 760 mL THF was added a solution of 4-bromoisoquinoline 24a (20 g, 96.6 mmol) in 144 mL THF dropwise at -65° C. and the resulting mixture was stirred at this temperature for another 30 mm after the completion of addition.
A solution of N-fluorobenzenesulfonimide (66.68 g, 211.7 mmol) in 216 mL THF was added at -65° C. in 1 h dropwisely.
After being stirred for another 1 h at this temperature, the reaction mixture was warmed to room temperature slowly with stirring, after the reaction is over, 300 mL saturated aq. NH4Cl was added slowly, extracted with EtOAc (300 mL*3).
The combined organic layers were washed with 300 mL brine, dried over anhydrous Na2SO4 and concentrated.
The crude product was purified by silica gel column chromatography (0-100percent EtOAc/PE) to give 4-fluoroisoquinoline 24b (8.5 g, red oil, yield: 60percent).
References: [1] Journal of the American Chemical Society, 2014, vol. 136, # 10, p. 3792 - 3795.
[2] Patent: US2017/37050, 2017, A1, . Location in patent: Paragraph 0301; 0302.
[3] Patent: US2007/179127, 2007, A1, . Location in patent: Page/Page column 47-48.
[4] Patent: US2009/48223, 2009, A1, . Location in patent: Page/Page column 101.
[5] Patent: US2010/93789, 2010, A1, . Location in patent: Page/Page column 46.
  • 2
  • [ 1532-97-4 ]
  • [ 7159-36-6 ]
References: [1] Journal of Organic Chemistry, 1957, vol. 22, p. 565.
 

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