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[ CAS No. 452-80-2 ] {[proInfo.proName]}

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Chemical Structure| 452-80-2
Chemical Structure| 452-80-2
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Product Details of [ 452-80-2 ]

CAS No. :452-80-2 MDL No. :MFCD00040975
Formula : C7H8FN Boiling Point : -
Linear Structure Formula :- InChI Key :ZQEXBVHABAJPHJ-UHFFFAOYSA-N
M.W : 125.14 Pubchem ID :67984
Synonyms :

Safety of [ 452-80-2 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P280-P305+P351+P338-P311 UN#:2810
Hazard Statements:H301+H311+H331-H315-H319-H335 Packing Group:Ⅲ
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Application In Synthesis of [ 452-80-2 ]

* 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.

  • Downstream synthetic route of [ 452-80-2 ]

[ 452-80-2 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 452-80-2 ]
  • [ 452-79-9 ]
YieldReaction ConditionsOperation in experiment
2.5 g (66%) With potassium iodide; sodium nitrite; In sulfuric acid; Preparation 8 3-Fluoro-4-iodotoluene (10a) To a suspension of 2-fluoro-4-methylaniline (2.0 g, 16 mmol) in aqueous sulfuric acid (~7 N) was added an aqueous solution of sodium nitrite (1.10 g, 16 mmol, 10 mL water) dropwise at 0 C. and the resulting light orange solution was stirred for 30 minutes. This solution was carefully poured into an aqueous solution of potassium iodide (3.98 g, 24 mmol, 16 mL water) at 80 C. and the resulting red mixture was stirred 1.5 hours at 80 C., and overnight at 50 C. The reaction was cooled to room temperature, poured into water (300 mL), and sodium bisulfite added until the light yellow color remained constant. The aqueous was extracted with diethyl ether (2*125 mL) and the organics were combined, washed with brine, dried (sodium sulfate), filtered, and the ether evaporated to give 2.5 g (66%) of crude product as a yellow green oil. Used without further purification. 1H NMR (CDCl3) delta2.32 (s, 3H,), 6.72 (dd, 1H, J=1.28 Hz, J=8.05 Hz), 6.88 (dd, 1H, J=1.28 Hz, JH=8.97 Hz), 7.58 (dd, 1H, J=1.08 Hz, J=6.78 Hz).
Step 7: The product from the previous step was dissolved in dry toluene (8mL) under argon. A portion of this stock solution (ImL) was added to a reaction-vial in a Mettler-Toledo Bohdan block using an atmosphere of argon to exclude air. 2-Fluoro-l-iodo-4-methyl-benzene (0.33mmol; prepared from 2-fluoro-4-methyl-phenylamine according to a general literature procedure [S. E. Tunney and J. K. Stille, J. Org. Chem., 52, 748-53 (1987)]) was added as a toluene solution (ImL) followed by 0.5mL of a freshly prepared toluene stock of solution of <n="18"/>tris(dibenzylideneacetone)dipalladium(0) (Pd2dba3) and bis[(2-diphenyl- phosphanyl)phenyl] ether DPEphos (corresponding to 0.3 equivalents palladium and 0.6 equivalents DPEphos). Potassium t°t-butoxide (0.66mmol) was added followed by tetra-n- butyl ammonium fluoride (TBAF; 1.0M in THF; 80 microliter). The mixture was stirred at 1000C overnight under argon. Next morning, the volatiles were removed using a Genevac instrument. The residue was dissolved in methanol (4mL) and loaded onto a VacMaster SCX- column (activated with 10% acetic acid in methanol). The product was eluted with acetonitrile. The volatiles were removed in vacuo. The residue was dissolved in methanol (1.5mL) and 4M HCl in diethyl ether (1.5mL) was added. The mixture was shaken at room temperature over the weekend before the volatiles were removed in vacuo. The residue was dissolved in dimethyl sulfoxide (0.18mL) and filtered. A few drops of 20% acetonitrile in water were added, and the mixture was filtered again. The product was isolated by preparative LC/MS as described, concentrated in vacuo, and the product was dissolved in dimethyl sulfoxide (0.78mL) to give a 1OmM solution. LC/MS-data: Method 14, retention time (UV) 2.152 min; UV-purity 79.5%; ELS-purity 100%; mass observed 337.407.
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