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Chemical Structure| 7569-58-6 Chemical Structure| 7569-58-6

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Chemical Structure| 7569-58-6

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Product Details of [ 7569-58-6 ]

CAS No. :7569-58-6
Formula : C9H8ClNO
M.W : 181.62
SMILES Code : N#CCC1=CC=C(OC)C(Cl)=C1
MDL No. :MFCD00068623
InChI Key :CDNWEVUZHGBTIV-UHFFFAOYSA-N
Pubchem ID :1502001

Safety of [ 7569-58-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H312-H315-H319-H332
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362-P403-P501

Application In Synthesis of [ 7569-58-6 ]

* 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 [ 7569-58-6 ]

[ 7569-58-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 4903-09-7 ]
  • [ 7569-58-6 ]
YieldReaction ConditionsOperation in experiment
83% With potassium tert-butylate; In tetrahydrofuran; methanol; water; Example 142-(3-Chloro-4-methoxyphenyl)acetonitrileTo a suspension of t-BuOK (4.8 g, 40 mmol) in THF (30 mL) was added a solution of TosMIC (3.9 g, 20 mmol) in THF (10 mL) at -78° C.The mixture was stirred for 10 minutes, treated with a solution of <strong>[4903-09-7]3-chloro-4-methoxy-benzaldehyde</strong> (1.7 g, 10 mmol) in THF (10 mL) dropwise, and continued to stir for 1.5 hours at -78° C.To the cooled reaction mixture was added methanol (10 mL).The mixture was heated at reflux for 30 minutes.Solvent of the reaction mixture was removed to give a crude product, which was dissolved in water (20 mL).The aqueous phase was extracted with EtOAc (20 mL*3).The combined organic layers were dried and evaporated under reduced pressure to give crude product, which was purified by column chromatography (petroleum ether/ethyl acetate 10:1) to afford 2-(3-chloro-4-methoxyphenyl)acetonitrile (1.5 g, 83percent).1H NMR (400 MHz, CDCl3) delta 7.33 (d, J=2.4 Hz, 1H), 7.20 (dd, J=2.4, 8.4 Hz, 1H), 6.92 (d, J=8.4 Hz, 1H), 3.91 (s, 3H), 3.68 (s, 2H).13C NMR (100 MHz, CDCl3) delta 154.8, 129.8, 127.3, 123.0, 122.7, 117.60, 112.4, 56.2, 22.4.
  • 2
  • [ 4903-09-7 ]
  • [ 38622-91-2 ]
  • [ 7569-58-6 ]
YieldReaction ConditionsOperation in experiment
83% To a suspension of t-BuOK (4.8 g, 40 mmol) in THF (30 mL) was added a solution of TosMIC (3.9 g, 20 mmol) in THF (10 mL) at -78° C. The mixture was stirred for 10 minutes, treated with a solution of <strong>[4903-09-7]3-chloro-4-methoxy-benzaldehyde</strong> (1.7 g, 10 mmol) in THF (10 mL) dropwise, and continued to stir for 1.5 hours at -78° C. To the cooled reaction mixture was added methanol (10 mL). The mixture was heated at reflux for 30 minutes. Solvent of the reaction mixture was removed to give a crude product, which was dissolved in water (20 mL). The aqueous phase was extracted with EtOAc (20 mL.x.3). The combined organic layers were dried and evaporated under reduced pressure to give crude product, which was purified by column chromatography (petroleum ether/ethyl acetate 10:1) to afford 2-(3-chloro-4-methoxyphenyl)acetonitrile (1.5 g, 83percent). 1H NMR (400 MHz, CDCl3) delta 7.33 (d, J=2.4 Hz, 1H), 7.20 (dd, J=2.4, 8.4 Hz, 1H), 6.92 (d, J=8.4 Hz, 1H), 3.91 (s, 3H), 3.68 (s, 2H). 13C NMR (100 MHz, CDCl3) delta 154.8, 129.8, 127.3, 123.0, 122.7, 117.60, 112.4, 56.2, 22.4.
83% To a suspension of t-BuOK (4.8 g, 40 mmol) in THF (30 mL) was added a solution of TosMIC (3.9 g, 20 mmol) in THF (10 mL) at -78° C. The mixture was stirred for 10 minutes, treated with a solution of <strong>[4903-09-7]3-chloro-4-methoxy-benzaldehyde</strong> (1.7 g, 10 mmol) in THF (10 mL) dropwise, and continued to stir for 1.5 hours at -78° C. To the cooled reaction mixture was added methanol (10 mL). The mixture was heated at reflux for 30 minutes. Solvent of the reaction mixture was removed to give a crude product, which was dissolved in water (20 mL). The aqueous phase was extracted with EtOAc (20 mL*3). The combined organic layers were dried and evaporated under reduced pressure to give crude product, which was purified by column chromatography (petroleum ether/ethyl acetate 10:1) to afford 2-(3-chloro-4-methoxyphenyl)acetonitrile (1.5 g, 83percent). 1H NMR (400 MHz, CDCl3) delta 7.33 (d, J=2.4 Hz, 1H), 7.20 (dd, J=2.4, 8.4 Hz, 1H), 6.92 (d, J=8.4 Hz, 1H), 3.91 (s, 3H), 3.68 (s, 2H). 13C NMR (100 MHz, CDCl3) delta 154.8, 129.8, 127.3, 123.0, 122.7, 117.60, 112.4, 56.2, 22.4.
83% E. 2-(3-Chloro-4-methoxyphenyl)acetonitrile; To a suspension of t-BuOK (4.8 g, 40 mmol) in THF (30 mL) was added a solution of TosMIC (3.9 g, 20 mmol) in THF (10 mL) at -78 0C and the mixture was stirred for 10 minutes. A solution of <strong>[4903-09-7]3-chloro-4-methoxy-benzaldehyde</strong> (1.7 g, 10 mmol) in THF (10 mL) was added dropwise, and the reaction was stirred at -78 0C for 1.5 hours. To the cooled reaction mixture was added methanol (10 mL) and the mixture was heated at reflux for 30 minutes. The solvent were evaporated to give a crude residue that was dissolved in water (20 mL). The aqueous phase was extracted with ethyl acetate (20 mL x 3). The combined organic layers were dried and evaporated under reduced pressure to give a crude product that was purified by column chromatography (petroleum ether/ethyl acetate 10: 1) to yield 2-(3-chloro-4- methoxyphenyl)acetonitrile (1.5 g, 83percent). 1H NMR (400 MHz, CDCl3) delta 7.33 (d, J= 2.4 Hz, 1 H), 7.20 (dd, J= 2.4, 8.4 Hz, 1 H), 6.92 (d, J= 8.4 Hz, 1 H), 3.91 (s, 3 H), 3.68 (s, 2 H). 13C NMR (100 MHz, CDCl3) delta 154.8, 129.8, 127.3, 123.0, 122.7, 117.60, 112.4, 56.2, 22.4.
 

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