No renderable structure data available
C1=CC=C(C=C1)COC(=O)C2=CC=CC=C2FChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | benzyl 2-fluorobenzoate |
|---|---|
| IUPAC Name | — |
| CAS Number | 478059-14-2 |
| Database ID | 579331 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
benzyl 2-fluorobenzoate (CAS 478059-14-2) 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 579331
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
8 reactions · 8 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-6089e0b60e0a432d9ba02d625a43e360Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirring solution of ethyl-N-hydroxyacetimidate (2.06 g, 20.0 mmol) in anhydrous DMF (60 mL) under Ar was added tBuOK (2.21 g, 19.7 mmol) all at once. After 30 min benzyl-2-fluorobenzoate 16 (4.13 g, 17.9 mmol) was added as a solution in DMF (20 mL) and the reaction was stirred at room temperature. After 3 h the reaction was diluted with H2O (400 mL), extracted with EtOAc (3×100 mL), and the combined organics were washed with H2O (3×50 mL) and brine (50 mL), dried over Na2SO4, filtered, and concentrated. Flash chromatographic purification over silica (5-10% gradient EtOAc in hexanes) afforded 18 as a clear syrup (3.61 g, 64%). 1H-NMR (500 MHz, CDCl3) δ 1.34 (t, J=7.0 Hz, 3H), 2.00 (s, 3H), 4.18 (q, J=7.0 Hz, 2H), 5.34 (s, 2H), 6.96 (dt, J=1.1, 7.7 Hz, 1H), 7.30-7.35 (m, 1H), 7.35-7.39 (m, 2H), 7.42-7.48 (m, 3H), 7.55 (dd, J=1.1, 8.4 Hz, 1H), 7.90 (dd, J=1.8, 7.7 Hz, 1H); 13C-NMR (125 MHz, CDCl3) δ 14.4, 14.5, 63.1, 66.6, 114.5, 117.0, 120.4, 128.2, 128.4, 128.5, 131.7, 133.8, 136.1, 159.5, 165.8, 166.7; GC-MS 313 m/z[M]+, C18H19NO4 requires 313, 228 m/z [M-85]+, benzyl-2-hydroxybenzoate C14H12O3 requires 228. extracted with EtOAc (3×100 mL) the combined organics were washed with H2O (3×50 mL) and brine (50 mL) dried over Na2SO4 filtered concentrated Flash chromatographic purification over silica (5-10% gradient EtOAc in hexanes)
Source ID: ord-f6c3789309154a24a6e630df0462cb05Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Benzyl alcohol (4.05 mL, 39.1 mmol) was added slowly to a stirring solution of 4-fluorobenzoic acid (5.00 g, 35.7 mmol), 4-(dimethylamino)pyridine (432 mg, 3.53 mmol), and 1,3-dicyclohexylcarbodiimide (8.15 g, 39.5 mmol) in anhydrous CH2Cl2 at room temperature under an argon atmosphere. After 18 h the reaction was worked up according to procedures as outlined for the synthesis of 16. Flash chromatographic purification over silica (10% EtOAc in hexanes) afforded 17 as a clear, colorless liquid (7.75 g, 94%). 1H-NMR (500 MHz, CDCl3) δ 5.35 (s, 2H), 7.06-14 (m, 2H), 7.32-7.41 (m, 3H), 7.41-7.47 (m, 2H), 8.06-8.12 (m, 2H); 13C-NMR (125 MHz, CDCl3) δ 66.84, 115.5 (d, JC-F=22.0 Hz), 126.4 (d, JC-F=2.9 Hz), 128.2, 128.3, 128.6, 132.3 (d, JC-F=9.6 Hz), 135.9, 165.5, 165.8 (d, JC-F=253 Hz); GC-MS 230 m/z [M]+, C14H11OF2 requires 230. Flash chromatographic purification over silica (10% EtOAc in hexanes)
Source ID: ord-a396c85958c94bddb6beda696e2d32d5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Benzyl alcohol (2.60 mL, 25.1 mmol) was added slowly to a stirring solution of 2-fluorobenzoic acid (2.92 g, 20.8 mmol), 4-(dimethylamino)pyridine (251 mg, 2.05 mmol), and 1,3-dicyclohexylcarbodiimide (5.16 g, 25.0 mmol) in anhydrous CH2Cl2 at room temperature under an Ar atmosphere. After 18 h the precipitate was filtered off and washed with CH2Cl2, and the filtrate was concentrated with silica to a powder. Flash chromatographic purification over silica (10% to 20% gradient EtOAc in hexanes) afforded 16 as a clear, colorless liquid (4.20 g, 88%). 1H-NMR (500 MHz, CDCl3) δ 5.39 (s, 2H), 7.14 (ddd, J=1.1, 8.4, 9.5 Hz, 1H), 7.20 (dt, J=1.1, 7.7 Hz, 1H), 7.31-7.36 (m, 1H), 7.37-7.41 (m, 2H), 7.44-7.48 (m, 2H), 7.49-7.55 (m, 1H), 7.96 (dt, J=1.8, 7.3 Hz); 13C-NMR (125 MHz, CDCl3) δ 66.93, 117.0 (d, JC-F=22.1 Hz), 118.7 (d, JC-F=9.6 Hz), 124.0 (d, JC-F=3.8 Hz), 128.1, 128.2, 128.6, 132.2, 134.6 (d, JC-F=9.6 Hz), 135.7, 162.1 (d, JC-F=260 Hz), 164.2 (d, JC-F=3.8 Hz); GC-MS 230 m/z [M]+, C14H11OF2 requires 230. After 18 h the precipitate was filtered off washed with CH2Cl2 the filtrate was concentrated with silica to a powder Flash chromatographic purification over silica (10% to 20% gradient EtOAc in hexanes)
Source ID: ord-ddd22656f89a43aa8232f91cf65698b3Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-6089e0b60e0a432d9ba02d625a43e360Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirring solution of ethyl-N-hydroxyacetimidate (2.06 g, 20.0 mmol) in anhydrous DMF (60 mL) under Ar was added tBuOK (2.21 g, 19.7 mmol) all at once. After 30 min benzyl-2-fluorobenzoate 16 (4.13 g, 17.9 mmol) was added as a solution in DMF (20 mL) and the reaction was stirred at room temperature. After 3 h the reaction was diluted with H2O (400 mL), extracted with EtOAc (3×100 mL), and the combined organics were washed with H2O (3×50 mL) and brine (50 mL), dried over Na2SO4, filtered, and concentrated. Flash chromatographic purification over silica (5-10% gradient EtOAc in hexanes) afforded 18 as a clear syrup (3.61 g, 64%). 1H-NMR (500 MHz, CDCl3) δ 1.34 (t, J=7.0 Hz, 3H), 2.00 (s, 3H), 4.18 (q, J=7.0 Hz, 2H), 5.34 (s, 2H), 6.96 (dt, J=1.1, 7.7 Hz, 1H), 7.30-7.35 (m, 1H), 7.35-7.39 (m, 2H), 7.42-7.48 (m, 3H), 7.55 (dd, J=1.1, 8.4 Hz, 1H), 7.90 (dd, J=1.8, 7.7 Hz, 1H); 13C-NMR (125 MHz, CDCl3) δ 14.4, 14.5, 63.1, 66.6, 114.5, 117.0, 120.4, 128.2, 128.4, 128.5, 131.7, 133.8, 136.1, 159.5, 165.8, 166.7; GC-MS 313 m/z[M]+, C18H19NO4 requires 313, 228 m/z [M-85]+, benzyl-2-hydroxybenzoate C14H12O3 requires 228. extracted with EtOAc (3×100 mL) the combined organics were washed with H2O (3×50 mL) and brine (50 mL) dried over Na2SO4 filtered concentrated Flash chromatographic purification over silica (5-10% gradient EtOAc in hexanes)
Source ID: ord-f6c3789309154a24a6e630df0462cb05Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Benzyl alcohol (4.05 mL, 39.1 mmol) was added slowly to a stirring solution of 4-fluorobenzoic acid (5.00 g, 35.7 mmol), 4-(dimethylamino)pyridine (432 mg, 3.53 mmol), and 1,3-dicyclohexylcarbodiimide (8.15 g, 39.5 mmol) in anhydrous CH2Cl2 at room temperature under an argon atmosphere. After 18 h the reaction was worked up according to procedures as outlined for the synthesis of 16. Flash chromatographic purification over silica (10% EtOAc in hexanes) afforded 17 as a clear, colorless liquid (7.75 g, 94%). 1H-NMR (500 MHz, CDCl3) δ 5.35 (s, 2H), 7.06-14 (m, 2H), 7.32-7.41 (m, 3H), 7.41-7.47 (m, 2H), 8.06-8.12 (m, 2H); 13C-NMR (125 MHz, CDCl3) δ 66.84, 115.5 (d, JC-F=22.0 Hz), 126.4 (d, JC-F=2.9 Hz), 128.2, 128.3, 128.6, 132.3 (d, JC-F=9.6 Hz), 135.9, 165.5, 165.8 (d, JC-F=253 Hz); GC-MS 230 m/z [M]+, C14H11OF2 requires 230. Flash chromatographic purification over silica (10% EtOAc in hexanes)
Source ID: ord-a396c85958c94bddb6beda696e2d32d5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Benzyl alcohol (2.60 mL, 25.1 mmol) was added slowly to a stirring solution of 2-fluorobenzoic acid (2.92 g, 20.8 mmol), 4-(dimethylamino)pyridine (251 mg, 2.05 mmol), and 1,3-dicyclohexylcarbodiimide (5.16 g, 25.0 mmol) in anhydrous CH2Cl2 at room temperature under an Ar atmosphere. After 18 h the precipitate was filtered off and washed with CH2Cl2, and the filtrate was concentrated with silica to a powder. Flash chromatographic purification over silica (10% to 20% gradient EtOAc in hexanes) afforded 16 as a clear, colorless liquid (4.20 g, 88%). 1H-NMR (500 MHz, CDCl3) δ 5.39 (s, 2H), 7.14 (ddd, J=1.1, 8.4, 9.5 Hz, 1H), 7.20 (dt, J=1.1, 7.7 Hz, 1H), 7.31-7.36 (m, 1H), 7.37-7.41 (m, 2H), 7.44-7.48 (m, 2H), 7.49-7.55 (m, 1H), 7.96 (dt, J=1.8, 7.3 Hz); 13C-NMR (125 MHz, CDCl3) δ 66.93, 117.0 (d, JC-F=22.1 Hz), 118.7 (d, JC-F=9.6 Hz), 124.0 (d, JC-F=3.8 Hz), 128.1, 128.2, 128.6, 132.2, 134.6 (d, JC-F=9.6 Hz), 135.7, 162.1 (d, JC-F=260 Hz), 164.2 (d, JC-F=3.8 Hz); GC-MS 230 m/z [M]+, C14H11OF2 requires 230. After 18 h the precipitate was filtered off washed with CH2Cl2 the filtrate was concentrated with silica to a powder Flash chromatographic purification over silica (10% to 20% gradient EtOAc in hexanes)
Source ID: ord-ddd22656f89a43aa8232f91cf65698b3PubChem References
These sources are listed in the compound's public database record.
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