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COC1=CC(=CC(=C1N)OC)BrChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 4-bromo-2,6-dimethoxyaniline |
|---|---|
| IUPAC Name | — |
| CAS Number | 23957-21-3 |
| Database ID | 329423 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
4-bromo-2,6-dimethoxyaniline (CAS 23957-21-3) 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 329423
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-f8d9f4142d4544a29caf81d4ffc54bc2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of sodium nitrite (97 mg) in water (2.0 mL) was added dropwise to an ice-cold suspension of 4-bromo-2,6-dimethoxyaniline (232 mg) in 6.0 M hydrochloric acid (2.5 mL). After stirring in ice for 30 minutes, a solution of cupric chloride (495 mg) in concentrated hydrochloric acid (2.0 mL) was added. The reaction mixture was stirred at room temperature for 30 minutes, then at 100° C. for 2 hours, and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate and water, dried over anhydrous sodium sulfate, and evaporated. The residue was subjected to a column of silica gel using hexane-ethyl acetate (10:1) as an eluent to give the title compound as white powder. The reaction mixture was stirred at room temperature for 30 minutes at 100° C. for 2 hours extracted with ethyl acetate The organic layer was washed with a saturated aqueous sodium hydrogencarbonate and water dried over anhydrous sodium sulfate evaporated
Source ID: ord-2a9a4d48a69844f8bc084d1294484763Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of sodium nitrite (97 mg) in water (2.0 mL) was added dropwise to an ice-cold suspension of 4-bromo-2,6-dimethoxyaniline (232 mg) in 6.0 M hydrochloric acid (2.5 mL). After stirring in ice for 30 minutes, a solution of cupric chloride (495 mg) in concentrated hydrochloric acid (2.0 mL) was added. The reaction mixture was stirred at room temperature for 30 minutes, then at 100° C. for 2 hours, and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate and water, dried over anhydrous sodium sulfate, and evaporated. The residue was subjected to a column of silica gel using hexane-ethyl acetate (10:1) as an eluent to give the title compound as white powder. The reaction mixture was stirred at room temperature for 30 minutes at 100° C. for 2 hours extracted with ethyl acetate The organic layer was washed with a saturated aqueous sodium hydrogencarbonate and water dried over anhydrous sodium sulfate evaporated
Source ID: ord-21114d5cb17646b4a3b7a2690fb82b3aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of the crude 5-bromo-1,3-dimethoxy-2-amino-benzene from above and triethylamine (1.5 g, 15 mmol) in anhydrous dichloromethane (50 mL) was added dropwise tert-butyl acetyl chloride (1.6 g, 12 mmol) with stirring at room temperature. The reaction mixture was stirred for 3 hours at room temperature. Then the reaction mixture was diluted with dichloromethane, washed with water, dried over anhydrous sodium sulfate, and evaporated to dryness under reduced pressure. The residue was purified by silica gel column (ISCO, hexane/EtOAc, 0-40%, 40 min) to give a white solid (3.0 g, 91%). 1H-NMR (DMSO-d6, 400 MHz): δ 8.69 (brs, 1H, exchangeable with D20), 6.87 (s, 2H), 3.73 (s, 6H), 2.11 (s, 2H), 1.02 (s, 9H). The reaction mixture was stirred for 3 hours at room temperature washed with water dried over anhydrous sodium sulfate evaporated to dryness under reduced pressure The residue was purified by silica gel column (ISCO, hexane/EtOAc, 0-40%, 40 min)
Source ID: ord-59cb6c3e93094a428531bc36b591f3f5Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 5-Bromo-1,3-dimethoxy-2-nitro-benzene (2.6 g, 10 mmol) was dissolved in 200 mL of methanol and 40 mL of water was added, followed by 2.5 g of Fe powder and 2.5 g of ammonium chloride. The mixture was heated to reflux at 80° C. for 2 hours and the cooled reaction mixture was filtered and washed with methanol. The filtrate was evaporated under reduce pressure to give the crude product, which was used for next step without further purification. The mixture was heated the cooled reaction mixture was filtered washed with methanol The filtrate was evaporated
Source ID: ord-d6f8c24b10e849fab395758547fb5f8cConditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 5-Bromo-1,3-dimethoxy-2-nitro-benzene (2.6 g, 10 mmol) was dissolved in 200 mL of methanol and 40 mL of water was added, followed by 2.5 g of Fe powder and 2.5 g of ammonium chloride. The mixture was heated to reflux at 80° C. for 2 hours and the cooled reaction mixture was filtered and washed with methanol. The filtrate was evaporated under reduce pressure to give the crude product, which was used for next step without further purification. The mixture was heated the cooled reaction mixture was filtered washed with methanol The filtrate was evaporated
Source ID: ord-d6f8c24b10e849fab395758547fb5f8cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of sodium nitrite (97.0 mg, 1.40 mmol) in water (2.0 mL) was added dropwise to an ice-cold suspension of 4-bromo-2,6-dimethoxyaniline (Z. Naturforsch., B24(5), 524–527 (1969)) (232.0 mg, 1.00 mmol) in 6.0 M hydrochloric acid (2.5 mL). After stirring in ice for 30 minutes, a solution of cupric chloride (495.0 mg, 5.00 mmol) in concentrated hydrochloric acid (2.0 mL) was added. The reaction mixture was stirred at room temperature for 30 minutes and at 100° C. for 2 hours, and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate and water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to yield 1-bromo-4-chloro-3,5-dimethoxybenzene as a colorless amorphous powder (230.0 mg, yield: 92%). The reaction mixture was stirred at room temperature for 30 minutes and at 100° C. for 2 hours extracted with ethyl acetate The organic layer was washed with a saturated aqueous sodium hydrogencarbonate and water dried over anhydrous sodium sulfate concentrated under reduced pressure The residue was purified by column chromatography on silica gel
Source ID: ord-dad8d9854ba84a2893fc35baf51bb3fbConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of sodium nitrite (97.0 mg, 1.40 mmol) in water (2.0 mL) was added dropwise to an ice-cold suspension of 4-bromo-2,6-dimethoxyaniline (Z. Naturforsch., B24(5), 524–527 (1969)) (232.0 mg, 1.00 mmol) in 6.0 M hydrochloric acid (2.5 mL). After stirring in ice for 30 minutes, a solution of cupric chloride (495.0 mg, 5.00 mmol) in concentrated hydrochloric acid (2.0 mL) was added. The reaction mixture was stirred at room temperature for 30 minutes and at 100° C. for 2 hours, and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate and water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to yield 1-bromo-4-chloro-3,5-dimethoxybenzene as a colorless amorphous powder (230.0 mg, yield: 92%). The reaction mixture was stirred at room temperature for 30 minutes and at 100° C. for 2 hours extracted with ethyl acetate The organic layer was washed with a saturated aqueous sodium hydrogencarbonate and water dried over anhydrous sodium sulfate concentrated under reduced pressure The residue was purified by column chromatography on silica gel
Source ID: ord-dad8d9854ba84a2893fc35baf51bb3fbConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of sodium nitrite (97 mg) in water (2.0 mL) was added dropwise to an ice-cold suspension of 4-bromo-2,6-dimethoxyaniline (232 mg) in 6.0 M hydrochloric acid (2.5 mL). After stirring in ice for 30 minutes, a solution of cupric chloride (495 mg) in concentrated hydrochloric acid (2.0 mL) was added. The reaction mixture was stirred at room temperature for 30 minutes, then at 100° C. for 2 hours, and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate and water, dried over anhydrous sodium sulfate, and evaporated. The residue was subjected to a column of silica gel using hexane-ethyl acetate (10:1) as an eluent to give the title compound as white powder. The reaction mixture was stirred at room temperature for 30 minutes at 100° C. for 2 hours extracted with ethyl acetate The organic layer was washed with a saturated aqueous sodium hydrogencarbonate and water dried over anhydrous sodium sulfate evaporated
Source ID: ord-2a9a4d48a69844f8bc084d1294484763Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of sodium nitrite (97.0 mg, 1.40 mmol) in water (2.0 mL) was added dropwise to an ice-cold suspension of 4-bromo-2,6-dimethoxyaniline (Z. Naturforsch., B24(5), 524-527 (1969)) (232.0 mg, 1.00 mmol) in 6.0 M hydrochloric acid (2.5 mL). After stirring in ice for 30 minutes, a solution of cupric chloride (495.0 mg, 5.00 mmol) in concentrated hydrochloric acid (2.0 mL) was added. The reaction mixture was stirred at room temperature for 30 minutes and at 100° C. for 2 hours, and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate and water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to yield 1-bromo-4-chloro-3,5-dimethoxybenzene as a colorless amorphous powder (230.0 mg, yield: 92%). The reaction mixture was stirred at room temperature for 30 minutes and at 100° C. for 2 hours extracted with ethyl acetate The organic layer was washed with a saturated aqueous sodium hydrogencarbonate and water dried over anhydrous sodium sulfate concentrated under reduced pressure The residue was purified by column chromatography on silica gel
Source ID: ord-f08cb50cadf44c35b45d9834983c202cConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-f8d9f4142d4544a29caf81d4ffc54bc2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of sodium nitrite (97.0 mg, 1.40 mmol) in water (2.0 mL) was added dropwise to an ice-cold suspension of 4-bromo-2,6-dimethoxyaniline (Z. Naturforsch., B24(5), 524-527 (1969)) (232.0 mg, 1.00 mmol) in 6.0 M hydrochloric acid (2.5 mL). After stirring in ice for 30 minutes, a solution of cupric chloride (495.0 mg, 5.00 mmol) in concentrated hydrochloric acid (2.0 mL) was added. The reaction mixture was stirred at room temperature for 30 minutes and at 100° C. for 2 hours, and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate and water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to yield 1-bromo-4-chloro-3,5-dimethoxybenzene as a colorless amorphous powder (230.0 mg, yield: 92%). The reaction mixture was stirred at room temperature for 30 minutes and at 100° C. for 2 hours extracted with ethyl acetate The organic layer was washed with a saturated aqueous sodium hydrogencarbonate and water dried over anhydrous sodium sulfate concentrated under reduced pressure The residue was purified by column chromatography on silica gel
Source ID: ord-f08cb50cadf44c35b45d9834983c202cPubChem References
These sources are listed in the compound's public database record.
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