No renderable structure data available
CCOC(=O)C1=C(C=C(C=C1)F)OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | ethyl 4-fluoro-2-hydroxybenzoate |
|---|---|
| IUPAC Name | — |
| CAS Number | 1737-21-9 |
| Database ID | 22478444 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
ethyl 4-fluoro-2-hydroxybenzoate (CAS 1737-21-9) 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 22478444
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-9443ebb010184383947801eddc428e26Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-c3fa8b6a388847e8bb0ea1b2be6bd34fConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 4-fluoro-2-hydroxybenzoic acid ethyl ester (3.5 g) in dichloromethane (30 ml) were added N,N-diisopropylethylamine (5.0 g) and (chloromethyl)methyl ether (2.3 g) at 0° C., and this reaction mixture was stirred at room temperature overnight. This reaction mixture was poured into water, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate) to give the title compound (2.8 g). the resulting mixture was extracted with ethyl acetate The organic layer was washed with water and brine dried over anhydrous magnesium sulfate The solvent was removed under reduced pressure The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate)
Source ID: ord-924d891c5487441d8952fc3b428be366Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 4-fluoro-2-hydroxybenzoic acid (3.0 g) in ethanol (40 mL) was added thionyl chloride (5.61 mL) at 0° C., and the mixture was heated under reflux for 24 hours. The reaction mixture was concentrated under reduced pressure. This residue was poured into water, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the title compound (3.5 g). the mixture was heated under reflux for 24 hours The reaction mixture was concentrated under reduced pressure This residue was poured into water the resulting mixture was extracted with ethyl acetate The organic layer was washed with water and brine dried over anhydrous magnesium sulfate The solvent was removed under reduced pressure
Source ID: ord-44a4552d5f604378ae32d52257604492Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 4-fluoro-2-hydroxybenzoic acid (3.0 g) in ethanol (40 mL) was added thionyl chloride (5.61 mL) at 0° C., and the mixture was heated under reflux for 24 hours. The reaction mixture was concentrated under reduced pressure. This residue was poured into water, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the title compound (3.5 g). the mixture was heated under reflux for 24 hours The reaction mixture was concentrated under reduced pressure This residue was poured into water the resulting mixture was extracted with ethyl acetate The organic layer was washed with water and brine dried over anhydrous magnesium sulfate The solvent was removed under reduced pressure
Source ID: ord-44a4552d5f604378ae32d52257604492Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Ethyl 4-fluoro-2-hydroxybenzoate (10.2 g, 55 mmol)) was dissolved in n-heptane. Iodo monochloride (12 g, 74 mmol) was added dropwise at ambient temperature with stirring. After 1 h, water was added and then solid sodium sulfite in small portions until the suspension was decolourized. More n-heptane was added to clear solution and the phases separated. The organic phase was dried and concentrated. The product crystallized on cooling. It was collected by filtration and washed with cold n-heptane. The crude yield was 10 g. The product was a mixture of ethyl 4-fluoro-2-hydroxy-5-iodobenzoate (about 80%) and the 5 chloro analogue (about 20%). the phases separated The organic phase was dried concentrated The product crystallized on cooling It was collected by filtration washed with cold n-heptane a mixture of ethyl 4-fluoro-2-hydroxy-5-iodobenzoate (about 80%)
Source ID: ord-392531f8a74a464590ea1cf53c4b0602Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Ethyl 4-fluoro-2-hydroxybenzoate (10.2 g, 55 mmol)) was dissolved in n-heptane. Iodo monochloride (12 g, 74 mmol) was added dropwise at ambient temperature with stirring. After 1 h, water was added and then solid sodium sulfite in small portions until the suspension was decolourized. More n-heptane was added to clear solution and the phases separated. The organic phase was dried and concentrated. The product crystallized on cooling. It was collected by filtration and washed with cold n-heptane. The crude yield was 10 g. The product was a mixture of ethyl 4-fluoro-2-hydroxy-5-iodobenzoate (about 80%) and the 5 chloro analogue (about 20%). the phases separated The organic phase was dried concentrated The product crystallized on cooling It was collected by filtration washed with cold n-heptane a mixture of ethyl 4-fluoro-2-hydroxy-5-iodobenzoate (about 80%)
Source ID: ord-392531f8a74a464590ea1cf53c4b0602Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 4-Fluoro-2-hydroxy-benzoic acid (10.8 g, 0.07 mol), sodium acetate (6.9 g, 0.084 mol), ethyl iodide (55 g, 0.35 mol) and dimethylformamide was stirred at ambient temperature for 48 h. The mixture was poured into water and extracted with n-hexane. The solution was filtered through a plug of silica gel and evaporated. The residue was almost pure product and was used directly in the next step. Yield 10.2 g, 80%. extracted with n-hexane The solution was filtered through a plug of silica gel evaporated
Source ID: ord-a6030d59fcaa4c9899771ad49c5da344Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 4-fluoro-2-hydroxybenzoic acid (3.0 g) in ethanol (40 mL) was added thionyl chloride (5.61 mL) at 0° C., and this mixture was heated to reflux for 24 hours. This reaction mixture was concentrated, and this residue was poured into water, and this mixture was extracted with ethyl acetate. This organic layer was washed with water and brine, dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give 4-fluoro-2-hydroxybenzoic acid ethyl ester (3.5 g). To a solution of 4-fluoro-2-hydroxybenzoic acid ethyl ester (3.5 g) in dichloromethane (30 mL) were added N,N-diisopropylethylamine (5.0 g) and (chloromethyl)methyl ether (2.3 g) at 0° C., and this reaction mixture was stirred at room temperature overnight. This reaction mixture was poured into water, and the resulting mixture was extracted with ethyl acetate. This organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane) to give the title compound (2.8 g). the resulting mixture was extracted with ethyl acetate This organic layer was washed with water and brine dried over anhydrous magnesium sulfate The solvent was removed under reduced pressure The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane)
Source ID: ord-9ffa9609518d4fd3a43d330014b55848Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 4-fluoro-2-hydroxybenzoic acid (3.0 g) in ethanol (40 mL) was added thionyl chloride (5.61 mL) at 0° C., and this mixture was heated to reflux for 24 hours. This reaction mixture was concentrated, and this residue was poured into water, and this mixture was extracted with ethyl acetate. This organic layer was washed with water and brine, dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give 4-fluoro-2-hydroxybenzoic acid ethyl ester (3.5 g). To a solution of 4-fluoro-2-hydroxybenzoic acid ethyl ester (3.5 g) in dichloromethane (30 mL) were added N,N-diisopropylethylamine (5.0 g) and (chloromethyl)methyl ether (2.3 g) at 0° C., and this reaction mixture was stirred at room temperature overnight. This reaction mixture was poured into water, and the resulting mixture was extracted with ethyl acetate. This organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane) to give the title compound (2.8 g). this mixture was heated to reflux for 24 hours This reaction mixture was concentrated this residue was poured into water this mixture was extracted with ethyl acetate This organic layer was washed with water and brine dried over anhydrous magnesium sulfate The solvent was removed under reduced pressure
Source ID: ord-aeea05510e0a439c8dff17ff03e5a52cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 4-fluoro-2-hydroxybenzoic acid (3.0 g) in ethanol (40 mL) was added thionyl chloride (5.61 mL) at 0° C., and this mixture was heated to reflux for 24 hours. This reaction mixture was concentrated, and this residue was poured into water, and this mixture was extracted with ethyl acetate. This organic layer was washed with water and brine, dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give 4-fluoro-2-hydroxybenzoic acid ethyl ester (3.5 g). To a solution of 4-fluoro-2-hydroxybenzoic acid ethyl ester (3.5 g) in dichloromethane (30 mL) were added N,N-diisopropylethylamine (5.0 g) and (chloromethyl)methyl ether (2.3 g) at 0° C., and this reaction mixture was stirred at room temperature overnight. This reaction mixture was poured into water, and the resulting mixture was extracted with ethyl acetate. This organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane) to give the title compound (2.8 g). this mixture was heated to reflux for 24 hours This reaction mixture was concentrated this residue was poured into water this mixture was extracted with ethyl acetate This organic layer was washed with water and brine dried over anhydrous magnesium sulfate The solvent was removed under reduced pressure
Source ID: ord-aeea05510e0a439c8dff17ff03e5a52cConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-9443ebb010184383947801eddc428e26PubChem References
These sources are listed in the compound's public database record.
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