No renderable structure data available
COC(=O)C1=C(C=CC(=C1)F)C#NChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | methyl 2-cyano-5-fluorobenzoate |
|---|---|
| IUPAC Name | — |
| CAS Number | 606080-43-7 |
| Database ID | 11984295 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
methyl 2-cyano-5-fluorobenzoate (CAS 606080-43-7) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 11984295
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-19442efcabf64f5d89f1ebd2483ff8e4Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-710b129f7391403ba0f1b3160bf43826Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-19442efcabf64f5d89f1ebd2483ff8e4Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 4.03 g (22.5 mmol) 21a and 60.0 ml dimethylsulphoxid were added 2.23 g (27.0 mmol) dimethylamine hydrochloride and 6.54 g (47.3 mmol) potassium carbonate. The reaction mixture was stirred for 15 h at 65° C. in an autoclave and was reduced with high vacuum rotation evaporator at 65° C. The residue was diluted with dichloromethane, washed twice with water. The combined water phases were extracted with dichloromethane. The combined dichloromethane phases were washed with diluted sodium hydrogen carbonate solution, dried with sodium sulphate and concentrated. The oily crude was purified by column chromatography and the desired product 21b was obtained in 89.0% yield (4.09 g, 20.0 mmol). was reduced with high vacuum rotation evaporator at 65° C The residue was diluted with dichloromethane washed twice with water The combined water phases were extracted with dichloromethane The combined dichloromethane phases were washed with diluted sodium hydrogen carbonate solution dried with sodium sulphate concentrated The oily crude was purified by column chromatography
Source ID: ord-c720d94ff3e747cbbd9ca6d092be579eConditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 4.03 g (22.5 mmol) 21a and 60.0 ml dimethylsulphoxid were added 2.23 g (27.0 mmol) dimethylamine hydrochloride and 6.54 g (47.3 mmol) potassium carbonate. The reaction mixture was stirred for 15 h at 65° C. in an autoclave and was reduced with high vacuum rotation evaporator at 65° C. The residue was diluted with dichloromethane, washed twice with water. The combined water phases were extracted with dichloromethane. The combined dichloromethane phases were washed with diluted sodium hydrogen carbonate solution, dried with sodium sulphate and concentrated. The oily crude was purified by column chromatography and the desired product 21b was obtained in 89.0% yield (4.09 g, 20.0 mmol). was reduced with high vacuum rotation evaporator at 65° C The residue was diluted with dichloromethane washed twice with water The combined water phases were extracted with dichloromethane The combined dichloromethane phases were washed with diluted sodium hydrogen carbonate solution dried with sodium sulphate concentrated The oily crude was purified by column chromatography
Source ID: ord-c720d94ff3e747cbbd9ca6d092be579eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred suspension of 16.0 g (96.9 mmol) 2-Cyano-5-fluoro-benzoic acid (Apollo) and 161 ml methanol were added 30.4 g (387.6 mmol) acetyl chloride drop wisely at 0° C. The reaction mixture was stirred over night, filtered and concentrated. The residue was diluted with dichloromethane, washed with diluted sodium hydrogen carbonate solution, dried with sodium sulphate and concentrated. The residue was purified by column chromatography (hexane:ethylacetate). The desired product 21a was obtained in 86.0 yield (14.9 g; 83.3 mmol) drop wisely at 0° C filtered concentrated The residue was diluted with dichloromethane washed with diluted sodium hydrogen carbonate solution dried with sodium sulphate concentrated The residue was purified by column chromatography (hexane:ethylacetate)
Source ID: ord-b4544c5bafe542a08fbebba62f443e07Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-710b129f7391403ba0f1b3160bf43826Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of methyl 2-cyano-5-fluorobenzoate (4.48 g, 25.0 mmol), 2-bromo-5-hydroxybenzaldehyde (5.03 g, 25.0 mmol), and potassium carbonate (4.14 g, 30.0 mmol) in N,N-dimethylformamide (50 mL) was stirred at 80° C. overnight. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography (chloroform) to give methyl 5-(4-bromo-3-formylphenoxy)-2-cyanobenzoate (5.35 g, 71%). the mixture was extracted with ethyl acetate The organic layer was washed with brine dried on anhydrous sodium sulfate The solvent was removed under reduced pressure the residue was purified by silica gel chromatography (chloroform)
Source ID: ord-b16bdd3ad28f4ad2a2678f5e9a5a03d0Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of methyl 2-cyano-5-fluorobenzoate (4.48 g, 25.0 mmol), 2-bromo-5-hydroxybenzaldehyde (5.03 g, 25.0 mmol), and potassium carbonate (4.14 g, 30.0 mmol) in N,N-dimethylformamide (50 mL) was stirred at 80° C. overnight. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography (chloroform) to give methyl 5-(4-bromo-3-formylphenoxy)-2-cyanobenzoate (5.35 g, 71%). the mixture was extracted with ethyl acetate The organic layer was washed with brine dried on anhydrous sodium sulfate The solvent was removed under reduced pressure the residue was purified by silica gel chromatography (chloroform)
Source ID: ord-342b5202b7d34cc3b50a4826bd7d1c81Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of methyl 2-cyano-5-fluorobenzoate (4.48 g, 25.0 mmol), 2-bromo-5-hydroxybenzaldehyde (5.03 g, 25.0 mmol), and potassium carbonate (4.14 g, 30.0 mmol) in N,N-dimethylformamide (50 mL) was stirred at 80° C. overnight. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography (chloroform) to give methyl 5-(4-bromo-3-formylphenoxy)-2-cyanobenzoate (5.35 g, 71%). the mixture was extracted with ethyl acetate The organic layer was washed with brine dried on anhydrous sodium sulfate The solvent was removed under reduced pressure the residue was purified by silica gel chromatography (chloroform)
Source ID: ord-012f543fe401434bbb8829f249004e63Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of methyl 2-cyano-5-fluorobenzoate (4.48 g, 25.0 mmol), 2-bromo-5-hydroxybenzaldehyde (5.03 g, 25.0 mmol), and potassium carbonate (4.14 g, 30.0 mmol) in N,N-dimethylformamide (50 mL) was stirred at 80° C. overnight. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography (chloroform) to give methyl 5-(4-bromo-3-formylphenoxy)-2-cyanobenzoate (5.35 g, 71%). the mixture was extracted with ethyl acetate The organic layer was washed with brine dried on anhydrous sodium sulfate The solvent was removed under reduced pressure the residue was purified by silica gel chromatography (chloroform)
Source ID: ord-657ac28275a54ce19c6138130e1f1ddfConditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 4.03 g (22.5 mmol) 21a and 60.0 ml dimethylsulphoxid were added 2.23 g (27.0 mmol) dimethylamine hydrochloride and 6.54 g (47.3 mmol) potassium carbonate. The reaction mixture was stirred for 15 h at 65° C. in an autoclave and was reduced with high vacuum rotation evaporator at 65° C. The residue was diluted with dichloromethane, washed twice with water. The combined water phases were extracted with dichloromethane. The combined dichloromethane phases were washed with diluted sodium hydrogen carbonate solution, dried with sodium sulphate and concentrated. The oily crude was purified by column chromatography and the desired product 21b was obtained in 89.0% yield (4.09 g, 20.0 mmol). was reduced with high vacuum rotation evaporator at 65° C The residue was diluted with dichloromethane washed twice with water The combined water phases were extracted with dichloromethane The combined dichloromethane phases were washed with diluted sodium hydrogen carbonate solution dried with sodium sulphate concentrated The oily crude was purified by column chromatography
Source ID: ord-c720d94ff3e747cbbd9ca6d092be579ePubChem References
These sources are listed in the compound's public database record.
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