No renderable structure data available
CCOC(=O)C1=CC(=CC=C1)FChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | ethyl 3-fluorobenzoate |
|---|---|
| IUPAC Name | — |
| CAS Number | 451-02-5 |
| Database ID | 67975 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
ethyl 3-fluorobenzoate (CAS 451-02-5) 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 67975
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-583311b8fdf7450ebdb501ea4eb73ca0Conditions: temp:80.01; pressure:0.00; stir:
Source ID: ord-21fd5ad70f2b45d7b267a6d6d00e149cConditions: temp:80.01; pressure:0.00; stir:
Source ID: ord-08ddf5ec2e6a40b3acf143be724c313bConditions: temp:60.01; pressure:0.00; stir:
Source ID: ord-175d1f64c5b245dc8b49e0a99856559aConditions: temp:50.01; pressure:0.00; stir:
Source ID: ord-dc692f6578e84a0da4beb225a0fc8babConditions: temp:50.01; pressure:0.00; stir:
Source ID: ord-8806275e9a12481eb728ad106eba28c6Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-583311b8fdf7450ebdb501ea4eb73ca0Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 5,6-Dihydro-cyclopenta[b]thiophen-4-one (2.1 g, 15.0 mmol) in 15 mL of THF was treated with NaH (60 percent, 1.5 g, 36 mmol). After the addition of 3-Fluoro-benzoic acid ethyl ester, the reaction mixture was heated at 100° C. for 8 hr. The solution was cooled to room temperature and poured into water. The resulting mixture was acidified with concentrated HCl and was added with ethyl acetate (70 mL). The organic layer was collected, brined, dried over MgSO4(s), and concentrated under reduced pressure. The resultant precipitate was collected and recrystallized from ethanol to provide the corresponding 5-(2-Fluoro-benzoyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one (0.56 g, 2.1 mmol) as brown solid in 14% yield. The solution was cooled to room temperature The organic layer was collected dried over MgSO4(s) concentrated under reduced pressure The resultant precipitate was collected recrystallized from ethanol
Source ID: ord-125e1d60fc284ebd8954e782ab38a94fConditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 5,6-Dihydro-cyclopenta[b]thiophen-4-one (2.1 g, 15.0 mmol) in 15 mL of THF was treated with NaH (60 percent, 1.5 g, 36 mmol). After the addition of 3-Fluoro-benzoic acid ethyl ester, the reaction mixture was heated at 100° C. for 8 hr. The solution was cooled to room temperature and poured into water. The resulting mixture was acidified with concentrated HCl and was added with ethyl acetate (70 mL). The organic layer was collected, brined, dried over MgSO4(s), and concentrated under reduced pressure. The resultant precipitate was collected and recrystallized from ethanol to provide the corresponding 5-(4-Fluoro-benzoyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one (0.56 g, 2.1 mmol) as brown solid in 14% yield. The solution was cooled to room temperature The organic layer was collected dried over MgSO4(s) concentrated under reduced pressure The resultant precipitate was collected recrystallized from ethanol
Source ID: ord-014725e0ad5d4b93b59d94c6860e9f65Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 5,6-Dihydro-cyclopenta[b]thiophen-4-one (2.1 g, 15.0 mmol) in 15 mL of THF was treated with NaH (60 percent, 1.5 g, 36 mmol). After the addition of 3-Fluoro-benzoic acid ethyl ester, the reaction mixture was heated at 100° C. for 8 hr. The solution was cooled to room temperature and poured into water. The resulting mixture was acidified with concentrated HCl and was added with ethyl acetate (70 mL). The organic layer was collected, brined, dried over MgSO4(s), and concentrated under reduced pressure. The resultant precipitate was collected and recrystallized from ethanol to provide the corresponding 5-(4-Fluoro-benzoyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one (0.56 g, 2.1 mmol) as brown solid in 14% yield. The solution was cooled to room temperature The organic layer was collected dried over MgSO4(s) concentrated under reduced pressure The resultant precipitate was collected recrystallized from ethanol
Source ID: ord-014725e0ad5d4b93b59d94c6860e9f65Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: s-Butyllithium (52 mL, 1.4 M in pentane, 72 mmol) was added at −78 C over 90 min. to a solution of p-Anisic acid (5 g, 33 mmol) and TMEDA (11 ml, 72 mmol) in THF (80 mL). After stirring for 15 min. ethyl 3-fluorobenzoate (5 mL, 40 mmol) was added in one portion. The reaction mixture was stirred for 15 min. then it was quenched with water (20 mL). The reaction mixture was then warmed to room temperature poured into water (1.5 L) 1N NaOH (30 ml) was added and the reaction mixture was then extracted with EtOAc. The extracts were discarded. The aqueous phase was then acidified with conc. HCl to pH 1 and extracted with EtOAc. Drying (Na2SO4) and concentration gave a residue which was recrystallized from hexanes/EtOAc to give the title compound as a white solid. was added in one portion it was quenched with water (20 mL) poured into water (1.5 L) 1N NaOH (30 ml) was added the reaction mixture was then extracted with EtOAc extracted with EtOAc Drying (Na2SO4) and concentration gave a residue which was recrystallized from hexanes/EtOAc
Source ID: ord-1764eb1921964e0188df4702d06cc015Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: s-Butyllithium (52 mL, 1.4 M in pentane, 72 mmol) was added at −78 C over 90 min. to a solution of p-Anisic acid (5 g, 33 mmol) and TMEDA (11 ml, 72 mmol) in THF (80 mL). After stirring for 15 min. ethyl 3-fluorobenzoate (5 mL, 40 mmol) was added in one portion. The reaction mixture was stirred for 15 min. then it was quenched with water (20 mL). The reaction mixture was then warmed to room temperature poured into water (1.5 L) 1N NaOH (30 ml) was added and the reaction mixture was then extracted with EtOAc. The extracts were discarded. The aqueous phase was then acidified with conc. HCl to pH 1 and extracted with EtOAc. Drying (Na2SO4) and concentration gave a residue which was recrystallized from hexanes/EtOAc to give the title compound as a white solid. was added in one portion it was quenched with water (20 mL) poured into water (1.5 L) 1N NaOH (30 ml) was added the reaction mixture was then extracted with EtOAc extracted with EtOAc Drying (Na2SO4) and concentration gave a residue which was recrystallized from hexanes/EtOAc
Source ID: ord-1764eb1921964e0188df4702d06cc015PubChem References
These sources are listed in the compound's public database record.
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