No renderable structure data available
CC1=C(C=CC(=C1)Br)OC(F)FChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 4-Bromo-1-(difluoromethoxy)-2-methylbenzene |
|---|---|
| IUPAC Name | — |
| CAS Number | 888327-32-0 |
| Database ID | 45158710 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
4-Bromo-1-(difluoromethoxy)-2-methylbenzene (CAS 888327-32-0) 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 45158710
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-ae778e093b224a81a3fc42448309eaedConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-3610792d2a8b4de2b3bd76d8e2bd3784Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-8f133474bd3b4b51ad5da2956d77a7b9Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-ae778e093b224a81a3fc42448309eaedConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-3610792d2a8b4de2b3bd76d8e2bd3784Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To 4-bromo-1-(difluoromethoxy)-2-methylbenzene (2.36 g, 10.00 mmol) in toluene (50 mL) was added cis-2,6-dimethylpiperazine (5 g, 58.14 mmol), Pd(OAc)2 (120 mg, 0.53 mmol), BINAP (380 mg, 0.61 mmol), and t-BuOK (2.2 g, 19.64 mmol). The resulting solution was stirred for 4 hours at 80° C. The solution was cooled to room temperature and washed with H2O (2×50 mL), dried over Na2SO4, concentrated, and purified by silica gel column chromatography (10:1 CH2Cl2/MeOH) to give 1.1 g (41%) of 1-(4-(difluoromethoxy)-3-methylphenyl)-3,5-dimethylpiperazine. The solution was cooled to room temperature washed with H2O (2×50 mL) dried over Na2SO4 concentrated purified by silica gel column chromatography (10:1 CH2Cl2/MeOH)
Source ID: ord-b2ae8fadf11640e3a132f402d609ade1Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 4-amino-1-difluoromethoxy-2-methyl-benzene (5 g, 28.90 mmol) in HBr (20 mL) and water (20 mL) at 0° C. was added a solution of sodium nitrite (2.07 g, 30.00 mmol) in H2O (10 ml) dropwise over a period of 20 minutes. After the addition was complete, the reaction mixture was stirred for 30 minutes at 0° C. Copper (I) bromide (4 g, 27.87 mmol) was then added and the mixture was heated at 60° C. for 30 minutes. The resulting solution was extracted with EtOAc (3×50 mL) and the combined organic layers washed with H2O (1×20 mL), dried over Na2SO4 and concentrated to provide 2.5 g (37%) of 4-bromo-1-(difluoromethoxy)-2-methylbenzene. After the addition the mixture was heated at 60° C. for 30 minutes The resulting solution was extracted with EtOAc (3×50 mL) the combined organic layers washed with H2O (1×20 mL) dried over Na2SO4 concentrated
Source ID: ord-64474ff9992e45518168107afa9f587cConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 4-amino-1-difluoromethoxy-2-methyl-benzene (5 g, 28.90 mmol) in HBr (20 mL) and water (20 mL) at 0° C. was added a solution of sodium nitrite (2.07 g, 30.00 mmol) in H2O (10 ml) dropwise over a period of 20 minutes. After the addition was complete, the reaction mixture was stirred for 30 minutes at 0° C. Copper (I) bromide (4 g, 27.87 mmol) was then added and the mixture was heated at 60° C. for 30 minutes. The resulting solution was extracted with EtOAc (3×50 mL) and the combined organic layers washed with H2O (1×20 mL), dried over Na2SO4 and concentrated to provide 2.5 g (37%) of 4-bromo-1-(difluoromethoxy)-2-methylbenzene. After the addition the mixture was heated at 60° C. for 30 minutes The resulting solution was extracted with EtOAc (3×50 mL) the combined organic layers washed with H2O (1×20 mL) dried over Na2SO4 concentrated
Source ID: ord-64474ff9992e45518168107afa9f587cConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-8f133474bd3b4b51ad5da2956d77a7b9Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To 4-bromo-1-(difluoromethoxy)-2-methylbenzene (2.36 g, 10.00 mmol) in toluene (50 mL) was added cis-2,6-dimethylpiperazine (5 g, 58.14 mmol), Pd(OAc)2 (120 mg, 0.53 mmol), BINAP (380 mg, 0.61 mmol), and t-BuOK (2.2 g, 19.64 mmol). The resulting solution was stirred for 4 hours at 80° C. The solution was cooled to room temperature and washed with H2O (2×50 mL), dried over Na2SO4, concentrated, and purified by silica gel column chromatography (10:1 CH2Cl2/MeOH) to give 1.1 g (41%) of 1-(4-(difluoromethoxy)-3-methylphenyl)-3,5-dimethylpiperazine. The solution was cooled to room temperature washed with H2O (2×50 mL) dried over Na2SO4 concentrated purified by silica gel column chromatography (10:1 CH2Cl2/MeOH)
Source ID: ord-5c3bc382159b40b384bb156f94513bb8Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 4-amino-1-difluoromethoxy-2-methyl-benzene (5 g, 28.90 mmol) in HBr (20 mL) and water (20 mL) at 0° C. was added a solution of sodium nitrite (2.07 g, 30.00 mmol) in H2O (10 ml) dropwise over a period of 20 minutes. After the addition was complete, the reaction mixture was stirred for 30 minutes at 0° C. Copper (I) bromide (4 g, 27.87 mmol) was then added and the mixture was heated at 60° C. for 30 minutes. The resulting solution was extracted with EtOAc (3×50 mL) and the combined organic layers washed with H2O (1×20 mL), dried over Na2SO4 and concentrated to provide 2.5 g (37%) of 4-bromo-1-(difluoromethoxy)-2-methylbenzene. After the addition the mixture was heated at 60° C. for 30 minutes The resulting solution was extracted with EtOAc (3×50 mL) the combined organic layers washed with H2O (1×20 mL) dried over Na2SO4 concentrated
Source ID: ord-53a4e676e9af458f8933b289d9414ad9Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To 4-bromo-1-(difluoromethoxy)-2-methylbenzene (2.36 g, 10.00 mmol) in toluene (50 mL) was added cis-2,6-dimethylpiperazine (5 g, 58.14 mmol), Pd(OAc)2 (120 mg, 0.53 mmol), BINAP (380 mg, 0.61 mmol), and t-BuOK (2.2 g, 19.64 mmol). The resulting solution was stirred for 4 hours at 80° C. The solution was cooled to room temperature and washed with H2O (2×50 mL), dried over Na2SO4, concentrated, and purified by silica gel column chromatography (10:1 CH2Cl2/MeOH) to give 1.1 g (41%) of 1-(4-(difluoromethoxy)-3-methylphenyl)-3,5-dimethylpiperazine. The solution was cooled to room temperature washed with H2O (2×50 mL) dried over Na2SO4 concentrated purified by silica gel column chromatography (10:1 CH2Cl2/MeOH)
Source ID: ord-d301260570764575b6df36e154dfc5aePubChem References
These sources are listed in the compound's public database record.
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