No renderable structure data available
C1CC(C(=O)C1)C2=CC(=CC(=C2)F)FChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 2-(3,5-difluorophenyl)cyclopentan-1-one |
|---|---|
| IUPAC Name | — |
| CAS Number | 1263869-51-7 |
| Database ID | 58075821 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
2-(3,5-difluorophenyl)cyclopentan-1-one (CAS 1263869-51-7) 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 58075821
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-3791c5b72d08488299ad83966ec00c31Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-3791c5b72d08488299ad83966ec00c31Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-3791c5b72d08488299ad83966ec00c31Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 2-(3,5-difluorophenyl)cyclopentanone (4.765 g, 24.29 mmol) and carbonisocyanatidic chloride (4.61 g, 43.7 mmol) was heated at 58° C. for 1 h and at 130° C. for 2 h. Upon cooling to room temperature, the reaction mixture was dissolved in ethyl acetate and washed with saturated aqueous solution of sodium bicarbonate. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulfate and filtered. The solvent was removed in vacuum and the residue was purified by column chromatography on silica gel to give 7-(3,5-difluorophenyl)-6,7-dihydrocyclopenta[e][1,3]oxazine-2,4(3H,5H)-dione (700 mg, 2.64 mmol, 10.87% yield). LC-MS (M+H)+=266.1. 1H NMR (500 MHz, CDCl3) δ ppm 8.79 (1H, br s), 6.68-6.86 (3H, m), 4.22 (1H, br s), 2.87 (1H, dt, J=7.0, 4.4 Hz), 2.63-2.82 (2H, m), 2.15 (1H, br s). Upon cooling to room temperature washed with saturated aqueous solution of sodium bicarbonate The organic layer was separated the aqueous layer was extracted with ethyl acetate The combined organic extracts were dried over anhydrous magnesium sulfate filtered The solvent was removed in vacuum the residue was purified by column chromatography on silica gel
Source ID: ord-0f6b71e7edc44fbd8e0344c737923b04Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 2-(3,5-difluorophenyl)cyclopentanone (4.765 g, 24.29 mmol) and carbonisocyanatidic chloride (4.61 g, 43.7 mmol) was heated at 58° C. for 1 h and at 130° C. for 2 h. Upon cooling to room temperature, the reaction mixture was dissolved in ethyl acetate and washed with saturated aqueous solution of sodium bicarbonate. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulfate and filtered. The solvent was removed in vacuum and the residue was purified by column chromatography on silica gel to give 7-(3,5-difluorophenyl)-6,7-dihydrocyclopenta[e][1,3]oxazine-2,4(3H,5H)-dione (700 mg, 2.64 mmol, 10.87% yield). LC-MS (M+H)+=266.1. 1H NMR (500 MHz, CDCl3) δ ppm 8.79 (1H, br s), 6.68-6.86 (3H, m), 4.22 (1H, br s), 2.87 (1H, dt, J=7.0, 4.4 Hz), 2.63-2.82 (2H, m), 2.15 (1H, br s). Upon cooling to room temperature washed with saturated aqueous solution of sodium bicarbonate The organic layer was separated the aqueous layer was extracted with ethyl acetate The combined organic extracts were dried over anhydrous magnesium sulfate filtered The solvent was removed in vacuum the residue was purified by column chromatography on silica gel
Source ID: ord-0f6b71e7edc44fbd8e0344c737923b04Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of (1S,2R)-2-(3,5-difluorophenyl)cyclopentanol (6 g, 30.3 mmol) in CH2Cl2 (150 mL) was added Dess-Martin periodinane (15.41 g, 36.3 mmol). The reaction mixture was stirred at rt for 3 h. The reaction mixture was diluted with dichloromethane and quenched with the addition of 1 N NaOH. The organic layer was collected, dried (Na2SO4) and concentrated. The crude product was purified by column chromatography on silica gel to afford 2-(3,5-difluorophenyl)cyclopentanone (4.765 g, 24.29 mmol, 80% yield). LC-MS (M+H)+=197.0. 1H NMR (500 MHz, CDCl3) δ ppm 6.70 (2H, d, J=6.7 Hz), 6.52-6.67 (1H, m), 3.17-3.33 (1H, m), 2.33-2.56 (2H, m), 2.06-2.26 (2H, m), 2.01 (1H, dd, J=11.7, 6.3 Hz), 1.89 (1H, br s). quenched with the addition of 1 N NaOH The organic layer was collected dried (Na2SO4) concentrated The crude product was purified by column chromatography on silica gel
Source ID: ord-aedb1083d951420aa748bbfeaf29e45cConditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 2-(3,5-difluorophenyl)cyclopentanone (4.765 g, 24.29 mmol) and carbonisocyanatidic chloride (4.61 g, 43.7 mmol) was heated at 58° C. for 1 h and at 130° C. for 2 h. Upon cooling to room temperature, the reaction mixture was dissolved in ethyl acetate and washed with saturated aqueous solution of sodium bicarbonate. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulfate and filtered. The solvent was removed in vacuum and the residue was purified by column chromatography on silica gel to give 7-(3,5-difluorophenyl)-6,7-dihydrocyclopenta[e][1,3]oxazine-2,4(3H,5H)-dione (700 mg, 2.64 mmol, 10.87% yield). LC-MS (M+H)+=266.1. 1H NMR (500 MHz, CDCl3) δ ppm 8.79 (1H, br s), 6.68-6.86 (3H, m), 4.22 (1H, br s), 2.87 (1H, dt, J=7.0, 4.4 Hz), 2.63-2.82 (2H, m), 2.15 (1H, br s). Upon cooling to room temperature washed with saturated aqueous solution of sodium bicarbonate The organic layer was separated the aqueous layer was extracted with ethyl acetate The combined organic extracts were dried over anhydrous magnesium sulfate filtered The solvent was removed in vacuum the residue was purified by column chromatography on silica gel
Source ID: ord-43731dfb1f3f4c0b858227e24a0c38a6Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of (1S,2R)-2-(3,5-difluorophenyl)cyclopentanol (6 g, 30.3 mmol) in CH2Cl2 (150 mL) was added Dess-Martin periodinane (15.41 g, 36.3 mmol). The reaction mixture was stirred at rt for 3 h. The reaction mixture was diluted with dichloromethane and quenched with the addition of 1 N NaOH. The organic layer was collected, dried (Na2SO4) and concentrated. The crude product was purified by column chromatography on silica gel to afford 2-(3,5-difluorophenyl)cyclopentanone (4.765 g, 24.29 mmol, 80% yield). LC-MS (M+H)+=197.0. 1H NMR (500 MHz, CDCl3) δ ppm 6.70 (2H, d, J=6.7 Hz), 6.52-6.67 (1H, m), 3.17-3.33 (1H, m), 2.33-2.56 (2H, m), 2.06-2.26 (2H, m), 2.01 (1H, dd, J=11.7, 6.3 Hz), 1.89 (1H, br s). quenched with the addition of 1 N NaOH The organic layer was collected dried (Na2SO4) concentrated The crude product was purified by column chromatography on silica gel
Source ID: ord-479a9eca749b4b2e932dab4e1a42366bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of (1S,2R)-2-(3,5-difluorophenyl)cyclopentanol (6 g, 30.3 mmol) in CH2Cl2 (150 mL) was added Dess-Martin periodinane (15.41 g, 36.3 mmol). The reaction mixture was stirred at rt for 3 h. The reaction mixture was diluted with dichloromethane and quenched with the addition of 1 N NaOH. The organic layer was collected, dried (Na2SO4) and concentrated. The crude product was purified by column chromatography on silica gel to afford 2-(3,5-difluorophenyl)cyclopentanone (4.765 g, 24.29 mmol, 80% yield). LC-MS (M+H)+=197.0. 1H NMR (500 MHz, CDCl3) δ ppm 6.70 (2H, d, J=6.7 Hz), 6.52-6.67 (1H, m), 3.17-3.33 (1H, m), 2.33-2.56 (2H, m), 2.06-2.26 (2H, m), 2.01 (1H, dd, J=11.7, 6.3 Hz), 1.89 (1H, br s). quenched with the addition of 1 N NaOH The organic layer was collected dried (Na2SO4) concentrated The crude product was purified by column chromatography on silica gel
Source ID: ord-479a9eca749b4b2e932dab4e1a42366bConditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 2-(3,5-difluorophenyl)cyclopentanone (4.765 g, 24.29 mmol) and carbonisocyanatidic chloride (4.61 g, 43.7 mmol) was heated at 58° C. for 1 h and at 130° C. for 2 h. Upon cooling to room temperature, the reaction mixture was dissolved in ethyl acetate and washed with saturated aqueous solution of sodium bicarbonate. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulfate and filtered. The solvent was removed in vacuum and the residue was purified by column chromatography on silica gel to give 7-(3,5-difluorophenyl)-6,7-dihydrocyclopenta[e][1,3]oxazine-2,4(3H,5H)-dione (700 mg, 2.64 mmol, 10.87% yield). LC-MS (M+H)+=266.1. 1H NMR (500 MHz, CDCl3) δ ppm 8.79 (1H, br s), 6.68-6.86 (3H, m), 4.22 (1H, br s), 2.87 (1H, dt, J=7.0, 4.4 Hz), 2.63-2.82 (2H, m), 2.15 (1H, br s). Upon cooling to room temperature washed with saturated aqueous solution of sodium bicarbonate The organic layer was separated the aqueous layer was extracted with ethyl acetate The combined organic extracts were dried over anhydrous magnesium sulfate filtered The solvent was removed in vacuum the residue was purified by column chromatography on silica gel
Source ID: ord-413af17ca2484f72b54f1665ce3d9a9cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of (1S,2R)-2-(3,5-difluorophenyl)cyclopentanol (6 g, 30.3 mmol) in CH2Cl2 (150 mL) was added Dess-Martin periodinane (15.41 g, 36.3 mmol). The reaction mixture was stirred at rt for 3 h. The reaction mixture was diluted with dichloromethane and quenched with the addition of 1 N NaOH. The organic layer was collected, dried (Na2SO4) and concentrated. The crude product was purified by column chromatography on silica gel to afford 2-(3,5-difluorophenyl)cyclopentanone (4.765 g, 24.29 mmol, 80% yield). LC-MS (M+H)+=197.0. 1H NMR (500 MHz, CDCl3) δ ppm 6.70 (2H, d, J=6.7 Hz), 6.52-6.67 (1H, m), 3.17-3.33 (1H, m), 2.33-2.56 (2H, m), 2.06-2.26 (2H, m), 2.01 (1H, dd, J=11.7, 6.3 Hz), 1.89 (1H, br s). quenched with the addition of 1 N NaOH The organic layer was collected dried (Na2SO4) concentrated The crude product was purified by column chromatography on silica gel
Source ID: ord-bdef4555c25e4534bf4ba31954e3302fConditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 2-(3,5-difluorophenyl)cyclopentanone (4.765 g, 24.29 mmol) and carbonisocyanatidic chloride (4.61 g, 43.7 mmol) was heated at 58° C. for 1 h and at 130° C. for 2 h. Upon cooling to room temperature, the reaction mixture was dissolved in ethyl acetate and washed with saturated aqueous solution of sodium bicarbonate. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulfate and filtered. The solvent was removed in vacuum and the residue was purified by column chromatography on silica gel to give 7-(3,5-difluorophenyl)-6,7-dihydrocyclopenta[e][1,3]oxazine-2,4(3H,5H)-dione (700 mg, 2.64 mmol, 10.87% yield). LC-MS (M+H)+=266.1. 1H NMR (500 MHz, CDCl3) δ ppm 8.79 (1H, br s), 6.68-6.86 (3H, m), 4.22 (1H, br s), 2.87 (1H, dt, J=7.0, 4.4 Hz), 2.63-2.82 (2H, m), 2.15 (1H, br s). Upon cooling to room temperature washed with saturated aqueous solution of sodium bicarbonate The organic layer was separated the aqueous layer was extracted with ethyl acetate The combined organic extracts were dried over anhydrous magnesium sulfate filtered The solvent was removed in vacuum the residue was purified by column chromatography on silica gel
Source ID: ord-0f6b71e7edc44fbd8e0344c737923b04PubChem References
These sources are listed in the compound's public database record.
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