No renderable structure data available
COC1=C(C=CC(=C1)Br)C(=O)ClChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 4-bromo-2-methoxybenzoyl chloride |
|---|---|
| IUPAC Name | — |
| CAS Number | 5213-16-1 |
| Database ID | 22346782 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
4-bromo-2-methoxybenzoyl chloride (CAS 5213-16-1) 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 22346782
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-81aef7774dd54e079e1a587eb437247aConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-fd3e0ef1499a4828b30f629ccc28998eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Phenethylamine (0.79 mL, 6.31 mmol) was added slowly to a mixture of 4-Bromo-2-methoxy-1-benzenecarbonyl chloride (1.5 g, 6.01 mmol) and triethylamine (1.3 mL, 9.02 mmol) in dichloromethane (60 mL). After 2 hours, solvent was removed under reduced pressure. Ethyl acetate was added and the mixture was filtered. The filtrate was concentrated under reduced pressure and the residue was purified by flash column chromatography using dichloromethane/ethyl acetate (97:3) as mobile to give N1-phenethyl-4-bromo-2-methoxybenzamide (1.81 g, 90%). 1H NMR (DMSO-d6) δ 2.83 (m, 2H), 3.50 (m, 2H), 3.84 (s, 3H), 7.31 (m, 7H), 7.65 (d, J=8.28 Hz, 1H), 8.15 (m, 1H). solvent was removed under reduced pressure Ethyl acetate was added the mixture was filtered The filtrate was concentrated under reduced pressure the residue was purified by flash column chromatography
Source ID: ord-a4ca78be4255462dacd821c99046e444Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Benzylamine (0.69 mL, 6.31 mmol) was added slowly to a mixture of 4-Bromo-2-methoxy-1-benzenecarbonyl chloride (1.5 g, 6.01 mmol) and triethylamine (1.3 mL, 9.02 mmol) in dichloromethane (60 mL). After 3 hours, solvent was removed under reduced pressure. Ethyl acetate was added and the mixture was filtered. The filtrate was concentrated under reduced pressure and the residue was re-crystallized from ethyl acetate/heptane to give N1-benzyl-4-bromo-2-methoxybenzamide (1.654 g, 86%). 1H NMR (DMSO-d6) δ 3.92 (s, 3H), 4.67 (d, J=5.67 Hz, 32H), 7.31 (m, 7H), 8.03 (bs, 1H), 8.13 (d, J=8.41, 1H). solvent was removed under reduced pressure Ethyl acetate was added the mixture was filtered The filtrate was concentrated under reduced pressure the residue was re-crystallized from ethyl acetate/heptane
Source ID: ord-1b67c27983a24c6bbc74483c19d92739Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Benzylamine (0.69 mL, 6.31 mmol) was added slowly to a mixture of 4-Bromo-2-methoxy-1-benzenecarbonyl chloride (1.5 g, 6.01 mmol) and triethylamine (1.3 mL, 9.02 mmol) in dichloromethane (60 mL). After 3 hours, solvent was removed under reduced pressure. Ethyl acetate was added and the mixture was filtered. The filtrate was concentrated under reduced pressure and the residue was re-crystallized from ethyl acetate/heptane to give N1-benzyl-4-bromo-2-methoxybenzamide (1.654 g, 86%). 1H NMR (DMSO-d6) δ 3.92 (s, 3H), 4.67 (d, J=5.67 Hz, 32H), 7.31 (m, 7H), 8.03 (bs, 1H), 8.13 (d, J=8.41, 1H). solvent was removed under reduced pressure Ethyl acetate was added the mixture was filtered The filtrate was concentrated under reduced pressure the residue was re-crystallized from ethyl acetate/heptane
Source ID: ord-1b67c27983a24c6bbc74483c19d92739Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Aniline(1.24 mL, 13.62 mmol) was added slowly to a mixture of 4-bromo-2-methoxy-1-benzenecarbonyl chloride (3.24 g, 12.98 mmol) and triethyl amine (2.7 mL, 19.48 mmol) in dichloromethane (130 mL). After 3 hours, solvent was removed under reduced pressure. Ethyl acetate was added and the mixture was filtered. The filtrate was concentrated under reduced pressure and the residue was re-crystallized from ethyl acetate/heptane to give N1-phenyl-4-bromo-2-methoxybenzamide (2.92 g, 74%). 1H NMR (DMSO-d6) δ 3.92 (s, 3H), 7.09 (s, 1H), 7.27 (m, 1H), 7.33 (m, 2H), 7.39 (s, 1H), 7.55 (d, J=8.15 Hz, 1H), 7.71 (m, 2H), 10.10 (s, 1H). solvent was removed under reduced pressure Ethyl acetate was added the mixture was filtered The filtrate was concentrated under reduced pressure the residue was re-crystallized from ethyl acetate/heptane
Source ID: ord-3a7b5fc6dc3f4b1f8a493b0e62d9bcf6Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Aniline(1.24 mL, 13.62 mmol) was added slowly to a mixture of 4-bromo-2-methoxy-1-benzenecarbonyl chloride (3.24 g, 12.98 mmol) and triethyl amine (2.7 mL, 19.48 mmol) in dichloromethane (130 mL). After 3 hours, solvent was removed under reduced pressure. Ethyl acetate was added and the mixture was filtered. The filtrate was concentrated under reduced pressure and the residue was re-crystallized from ethyl acetate/heptane to give N1-phenyl-4-bromo-2-methoxybenzamide (2.92 g, 74%). 1H NMR (DMSO-d6) δ 3.92 (s, 3H), 7.09 (s, 1H), 7.27 (m, 1H), 7.33 (m, 2H), 7.39 (s, 1H), 7.55 (d, J=8.15 Hz, 1H), 7.71 (m, 2H), 10.10 (s, 1H). solvent was removed under reduced pressure Ethyl acetate was added the mixture was filtered The filtrate was concentrated under reduced pressure the residue was re-crystallized from ethyl acetate/heptane
Source ID: ord-3a7b5fc6dc3f4b1f8a493b0e62d9bcf6Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 4-Bromo-2-methoxybenzoic acid (2.934 g, 12.70 mmol) was mixed with sodium carbonate (2.2 g, 26.51 mmol). Thionyl chloride (20 mL) was added and the reaction mixture was heated at 80° C. for 16 hours. After distilling off excess thionyl chloride, heptane was added and the solid was collected by filtration to give 4-bromo-2-methoxy-1-benzenecarbonyl chloride (3.16 g, 100%). 1H NMR (CDCl3) δ 3.94 (s, 3H), 7.16 (s, 1H), 7.20 (d, J=8.51 Hz, 1H), 7.95 (d, J=8.51 Hz, 1H). After distilling off excess thionyl chloride, heptane was added the solid was collected by filtration
Source ID: ord-ee2086572a44498f81b701af269e3d09Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a suspension of 4-bromo-2-methoxybenzoic acid (2.5 g, 11.04 mmol) in CHCl3 (20 mL) was added DMF (catalytic) and thionyl chloride (1.6 mL, 22.08 mmol). The reaction was stirred at 55° C. for 1 hour and then concentrated to dryness to give the title compound. concentrated to dryness
Source ID: ord-67b277e335884ebdaa425a295cfd4436Conditions: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a suspension of 4-bromo-2-methoxybenzoic acid (2.5 g, 11.04 mmol) in CHCl3 (20 mL) was added DMF (catalytic) and thionyl chloride (1.6 mL, 22.08 mmol). The reaction was stirred at 55° C. for 1 hour and then concentrated to dryness to give the title compound. concentrated to dryness
Source ID: ord-67b277e335884ebdaa425a295cfd4436Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Phenethylamine (0.79 mL, 6.31 mmol) was added slowly to a mixture of 4-Bromo-2-methoxy-1-benzenecarbonyl chloride (1.5 g, 6.01 mmol) and triethylamine (1.3 mL, 9.02 mmol) in dichloromethane (60 mL). After 2 hours, solvent was removed under reduced pressure. Ethyl acetate was added and the mixture was filtered. The filtrate was concentrated under reduced pressure and the residue was purified by flash column chromatography using dichloromethane/ethyl acetate (97:3) as mobile to give N1-phenethyl-4-bromo-2-methoxybenzamide (1.81 g, 90%). 1H NMR (DMSO-d6) δ 2.83 (m, 2H), 3.50 (m, 2H), 3.84 (s, 3H), 7.31 (m, 7H), 7.65 (d, J=8.28 Hz, 1H), 8.15 (m, 1H). solvent was removed under reduced pressure Ethyl acetate was added the mixture was filtered The filtrate was concentrated under reduced pressure the residue was purified by flash column chromatography
Source ID: ord-d07c2f44ff5d4c94920b1f54caec2816Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Benzylamine (0.69 mL, 6.31 mmol) was added slowly to a mixture of 4-Bromo-2-methoxy-1-benzenecarbonyl chloride (1.5 g, 6.01 mmol) and triethylamine (1.3 mL, 9.02 mmol) in dichloromethane (60 mL). After 3 hours, solvent was removed under reduced pressure. Ethyl acetate was added and the mixture was filtered. The filtrate was concentrated under reduced pressure and the residue was re-crystallized from ethyl acetate/heptane to give N1-benzyl-4-bromo-2-methoxybenzamide (1.654 g, 86%). 1H NMR (DMSO-d6) δ 3.92 (s, 3H), 4.67 (d, J=5.67 Hz, 32H), 7.31 (m, 7H), 8.03 (bs, 1H), 8.13 (d, J=8.41, 1H). solvent was removed under reduced pressure Ethyl acetate was added the mixture was filtered The filtrate was concentrated under reduced pressure the residue was re-crystallized from ethyl acetate/heptane
Source ID: ord-95e98ee7b1dc487b9121ab150653b6adPubChem References
These sources are listed in the compound's public database record.
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