No renderable structure data available
BrC1C=CC(CC(=O)OC)=CC=1FChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | Methyl 2-(4-bromo-3-fluorophenyl)acetate |
|---|---|
| IUPAC Name | — |
| CAS Number | 942282-41-9 |
| Database ID | 71265948 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
Methyl 2-(4-bromo-3-fluorophenyl)acetate (CAS 942282-41-9) 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 71265948
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-81a1669271bb499795223b55dc5b6cd4Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: (4-bromo-3-fluorophenyl)acetonitrile (40 g, 0.18 mol) was dissolved in 120 mL methanol, and 65 mL concentrated sulfuric acid were added. After heating at reflux overnight, the reaction mixture was cooled, and poured into 600 mL water, and the product was extracted with CH2Cl2. The combined extracts were washed with 10% sodium carbonate solution, dried, and concentrated to afford methyl (4-bromo-3-fluorophenyl)acetate. After heating at reflux overnight the reaction mixture was cooled the product was extracted with CH2Cl2 The combined extracts were washed with 10% sodium carbonate solution dried concentrated
Source ID: ord-c486df2e7ae841448520cfd8662d0b6aConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-81a1669271bb499795223b55dc5b6cd4Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a mixture of 2-(4-bromo-3-fluorophenyl)acetic acid (5 g, 21.46 mmol) in MeOH (50 mL) was added SOCl2 (1.879 mL, 25.7 mmol) and DMF (0.166 mL, 2.146 mmol). Then the mixture was stirred at 80° C. for 16 h. The mixture was concentrated and extracted with EA (100 mL×2) and washed with NaHCO3 (100 mL) to give the organic layer. The combined organic extract was washed with brine, dried over Na2SO4, filtered, and concentrated to yield a brown oil of methyl 2-(4-bromo-3-fluorophenyl)acetate (5 g, 17.20 mmol, 80% yield): 1H NMR (400 MHz, MeOH-d4) δ 7.53 (t, J=7.6 Hz, 1H), 7.15 (dd, J=1.6, 9.6 Hz, 1H), 7.04-6.99 (m, 1H), 3.67 (s, 3H), 3.65 (s, 2H); ES-LCMS m/z 249.0 (M+H+2). The mixture was concentrated extracted with EA (100 mL×2) washed with NaHCO3 (100 mL) to give the organic layer The combined organic extract was washed with brine dried over Na2SO4 filtered concentrated
Source ID: ord-e890bcbf76284227bf16cd26aedd0f4dConditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-(4-bromo-3-fluorophenyl)acetic acid (500 mg, 2.146 mmol) in MeOH (10 mL, 247 mmol) was added sulfurous dichloride (0.232 mL, 3.22 mmol). The resulting mixture was stirred at 60° C. After 3 h, LCMS analysis showed the starting material had disappeared and the solvent was removed in vacuo. The residue was dissolved in DCM (60 mL) and washed with aqueous NaHCO3 (20 mL) and brine (20 mL). The organic layer was dried over Na2SO4, filtered and concentrated to yield a yellow oil of methyl 2-(4-bromo-3-fluorophenyl)acetate (500 mg, 1.774 mmol, 83.0% yield): 1H NMR (400 MHz, CD3OD) δ 7.53 (t, J=8.0 Hz, 1H), 7.15 (dd, J=9.8, 1.7 Hz, 1H), 7.01 (d, J=8.2 Hz, 1H), 3.75-3.61 (m, 5H); ES-LCMS m/z 248.9 (M+H). the solvent was removed in vacuo The residue was dissolved in DCM (60 mL) washed with aqueous NaHCO3 (20 mL) and brine (20 mL) The organic layer was dried over Na2SO4 filtered concentrated
Source ID: ord-25ca1cd76efd4a5d8ce292b81196bb3dConditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-(4-bromo-3-fluorophenyl)acetic acid (500 mg, 2.146 mmol) in MeOH (10 mL, 247 mmol) was added sulfurous dichloride (0.232 mL, 3.22 mmol). The resulting mixture was stirred at 60° C. After 3 h, LCMS analysis showed the starting material had disappeared and the solvent was removed in vacuo. The residue was dissolved in DCM (60 mL) and washed with aq NaHCO3 (20 mL) and brine (20 mL). The organic layer was dried over Na2SO4, filtered and concentrated to yield a yellow oil of methyl 2-(4-bromo-3-fluorophenyl)acetate (500 mg, 1.774 mmol, 83.0% yield): 1H NMR (400 MHz, CD3OD) δ 7.53 (t, J=8.0 Hz, 1H), 7.15 (dd, J=9.8, 1.7 Hz, 1H), 7.01 (d, J=8.2 Hz, 1H), 3.75-3.61 (m, 5H); ES-LCMS m/z 248.9 (M+H). the solvent was removed in vacuo The residue was dissolved in DCM (60 mL) washed with aq NaHCO3 (20 mL) and brine (20 mL) The organic layer was dried over Na2SO4 filtered concentrated
Source ID: ord-32cbedc7adc54e469febfc88d421e094Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: (4-bromo-3-fluorophenyl)acetonitrile (40 g, 0.18 mol) was dissolved in 120 mL methanol, and 65 mL concentrated sulfuric acid were added. After heating at reflux overnight, the reaction mixture was cooled, and poured into 600 mL water, and the product was extracted with CH2Cl2. The combined extracts were washed with 10% sodium carbonate solution, dried, and concentrated to afford methyl (4-bromo-3-fluorophenyl)acetate. After heating at reflux overnight the reaction mixture was cooled the product was extracted with CH2Cl2 The combined extracts were washed with 10% sodium carbonate solution dried concentrated
Source ID: ord-c486df2e7ae841448520cfd8662d0b6aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: (4-bromo-3-fluorophenyl)acetonitrile (40 g, 0.18 mol) was dissolved in 120 mL methanol, and 65 mL concentrated sulfuric acid were added. After heating at reflux overnight, the reaction mixture was cooled, and poured into 600 mL water, and the product was extracted with CH2Cl2. The combined extracts were washed with 10% sodium carbonate solution, dried, and concentrated to afford methyl (4-bromo-3-fluorophenyl)acetate. After heating at reflux overnight the reaction mixture was cooled the product was extracted with CH2Cl2 The combined extracts were washed with 10% sodium carbonate solution dried concentrated
Source ID: ord-c486df2e7ae841448520cfd8662d0b6aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: (4-bromo-3-fluorophenyl)acetonitrile (40 g, 0.18 mol) was dissolved in 120 mL methanol, and 65 mL concentrated sulfuric acid were added. After heating at reflux overnight, the reaction mixture was cooled, and poured into 600 mL water, and the product was extracted with CH2Cl2. The combined extracts were washed with 10% sodium carbonate solution, dried, and concentrated to afford methyl (4-bromo-3-fluorophenyl)acetate. After heating at reflux overnight the reaction mixture was cooled the product was extracted with CH2Cl2 The combined extracts were washed with 10% sodium carbonate solution dried concentrated
Source ID: ord-1f802d86fc1f404a85dc2c82c04d1206Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-(4-bromo-3-fluorophenyl)acetic acid (500 mg, 2.146 mmol) in MeOH (10 mL, 247 mmol) was added sulfurous dichloride (0.232 mL, 3.22 mmol). The resulting mixture was stirred at 60° C. After 3 h, LCMS analysis showed the starting material had disappeared and the solvent was removed in vacuo. The residue was dissolved in DCM (60 mL) and washed with aq NaHCO3 (20 mL) and brine (20 mL). The organic layer was dried over Na2SO4, filtered and concentrated to yield a yellow oil of methyl 2-(4-bromo-3-fluorophenyl)acetate (500 mg, 1.774 mmol, 83.0% yield): 1H NMR (400 MHz, CD3OD) δ 7.53 (t, J=8.0 Hz, 1H), 7.15 (dd, J=9.8, 1.7 Hz, 1H), 7.01 (d, J=8.2 Hz, 1H), 3.75-3.61 (m, 5H); ES-LCMS m/z 248.9 (M+H). the solvent was removed in vacuo The residue was dissolved in DCM (60 mL) washed with aq NaHCO3 (20 mL) and brine (20 mL) The organic layer was dried over Na2SO4 filtered concentrated
Source ID: ord-f9b0d2df5986445babbb4562cf7dddf0Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a mixture of 2-(4-bromo-3-fluorophenyl)acetic acid (5 g, 21.46 mmol) in MeOH (50 mL) was added SOCl2 (1.879 mL, 25.7 mmol) and DMF (0.166 mL, 2.146 mmol). Then the mixture was stirred at 80° C. for 16 h. The mixture was concentrated and extracted with EA (100 mL×2) and washed with NaHCO3 (100 mL) to give the organic layer. The combined organic extract was washed with brine, dried over Na2SO4, filtered, and concentrated to yield a brown oil of methyl 2-(4-bromo-3-fluorophenyl)acetate (5 g, 17.20 mmol, 80% yield): 1H NMR (400 MHz, MeOH-d4) δ 7.53 (t, J=7.6 Hz, 1H), 7.15 (dd, J=1.6, 9.6 Hz, 1H), 7.04-6.99 (m, 1H), 3.67 (s, 3H), 3.65 (s, 2H); ES-LCMS m/z 249.0 (M+H+2). The mixture was concentrated extracted with EA (100 mL×2) washed with NaHCO3 (100 mL) to give the organic layer The combined organic extract was washed with brine dried over Na2SO4 filtered concentrated
Source ID: ord-e890bcbf76284227bf16cd26aedd0f4dConditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 2-(4-bromo-3-fluorophenyl)acetic acid (500 mg, 2.146 mmol) in MeOH (10 mL, 247 mmol) was added sulfurous dichloride (0.232 mL, 3.22 mmol). The resulting mixture was stirred at 60° C. After 3 h, LCMS analysis showed the starting material had disappeared and the solvent was removed in vacuo. The residue was dissolved in DCM (60 mL) and washed with aqueous NaHCO3 (20 mL) and brine (20 mL). The organic layer was dried over Na2SO4, filtered and concentrated to yield a yellow oil of methyl 2-(4-bromo-3-fluorophenyl)acetate (500 mg, 1.774 mmol, 83.0% yield): 1H NMR (400 MHz, CD3OD) δ 7.53 (t, J=8.0 Hz, 1H), 7.15 (dd, J=9.8, 1.7 Hz, 1H), 7.01 (d, J=8.2 Hz, 1H), 3.75-3.61 (m, 5H); ES-LCMS m/z 248.9 (M+H). the solvent was removed in vacuo The residue was dissolved in DCM (60 mL) washed with aqueous NaHCO3 (20 mL) and brine (20 mL) The organic layer was dried over Na2SO4 filtered concentrated
Source ID: ord-25ca1cd76efd4a5d8ce292b81196bb3dPubChem References
These sources are listed in the compound's public database record.
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