No renderable structure data available
CC(C)(C)OC(=O)N(C)C1=CC(=CC=C1)BrChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | tert-butyl N-(3-bromophenyl)-N-methylcarbamate |
|---|---|
| IUPAC Name | — |
| CAS Number | 57598-34-2 |
| Database ID | 22997148 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
tert-butyl N-(3-bromophenyl)-N-methylcarbamate (CAS 57598-34-2) 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 22997148
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-049af2c2003b44d9bd3bd87608e69df0Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-225a42da93494a98bda6a7cd2f3817a4Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 128 g (470 mmol) of tert-butyl 3-bromophenylcarbamate in 800 mL of dimethylformamide, 19 g (475 mmol) of sodium hydride (60% in oil) are added portionwise and the reaction medium is stirred until the evolution of gas has ceased. 29.3 mL (470 mmol) of methyl iodide are added dropwise and stirring is continued for 18 hours. The reaction medium is poured into ice-cold water and extracted with ethyl acetate. The organic phase is separated out after settling of the phases, dried over magnesium sulfate and evaporated. 152.5 g (92%) of tert-butyl 3-bromophenyl-N-methylcarbamate are obtained. stirring The reaction medium is poured into ice-cold water extracted with ethyl acetate The organic phase is separated out dried over magnesium sulfate evaporated
Source ID: ord-86a40377e43d4f53830c5f2b55ca051dConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 129 g (475 mmol) of tert-butyl (3-bromophenyl)carbamate in 800 mL of dimethylformamide are added portionwise 19 g (475 mmol) of sodium hydride (60% in oil) and the reaction medium is stirred until the evolution of gas has ceased. 29 mL (470 mmol) of methyl iodide are added dropwise and stirring is continued for 18 hours. The reaction medium is poured into ice-cold water and extracted with ethyl acetate. The organic phase is separated out after settling of the phases, dried over magnesium sulfate, filtered and evaporated. 115 g (95%) of tert-butyl (3-bromophenyl)-N-methylcarbamate are obtained. stirring The reaction medium is poured into ice-cold water extracted with ethyl acetate The organic phase is separated out dried over magnesium sulfate filtered evaporated
Source ID: ord-b599c5a53c194c918e2b35c552be0eb2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 114 g (447 mmol) of tert-butyl (3-bromophenyl)carbamate in 800 ml of DMF are added portionwise 19 g (475 mmol) of sodium hydride (60% in oil) and the reaction medium is stirred until the evolution of gas has ceased. 29.3 ml (470 mmol) of methyl iodide are added dropwise and stirring is continued for 18 hours. The reaction medium is poured into ice-cold water and extracted with ethyl acetate. The organic phase is separated out after settling of the phases, dried over magnesium sulfate and evaporated. 115 g of tert-butyl (3-bromophenyl)-N-methylcarbamate are obtained in a yield of 95%. stirring The reaction medium is poured into ice-cold water extracted with ethyl acetate The organic phase is separated out dried over magnesium sulfate evaporated
Source ID: ord-9e174b4906214e0bad73be36a5c81fc0Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 114 g (447 mmol) of tert-butyl (3-bromophenyl)carbamate in 800 ml of DMF are added portionwise 19 g (475 mmol) of sodium hydride (60% in oil) and the reaction medium is stirred until the evolution of gas has ceased. 29.3 ml (470 mmol) of methyl iodide are added dropwise and stirring is continued for 18 hours. The reaction medium is poured into ice-cold water and extracted with ethyl acetate. The organic phase is separated out after settling of the phases, dried over magnesium sulfate and evaporated. 115 g of tert-butyl (3-bromophenyl)-N-methylcarbamate are obtained in a yield of 95%. stirring The reaction medium is poured into ice-cold water extracted with ethyl acetate The organic phase is separated out dried over magnesium sulfate evaporated
Source ID: ord-9e174b4906214e0bad73be36a5c81fc0Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 114 g (447 mmol) of tert-butyl (3-bromophenyl)carbamate in 800 ml of DMF are added portionwise 19 g (475 mmol) of sodium hydride (60% in oil) and the reaction medium is stirred until the evolution of gas has ceased. 29.3 ml (470 mmol) of methyl iodide are added dropwise and stirring is continued for 18 hours. The reaction medium is poured into ice-water and extracted with ethyl acetate. The organic phase is separated out by settling of the phases, dried over magnesium sulfate and evaporated. 115 g of tert-butyl (3-bromophenyl)-N-methylcarbamate are obtained in a yield of 95%. stirring extracted with ethyl acetate The organic phase is separated out dried over magnesium sulfate evaporated
Source ID: ord-ba3433e1390b426396c07058c5da4ea4Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 114 g (447 mmol) of tert-butyl (3-bromophenyl)carbamate in 800 ml of DMF are added portionwise 19 g (475 mmol) of sodium hydride (60% in oil) and the reaction medium is stirred until the evolution of gas has ceased. 29.3 ml (470 mmol) of methyl iodide are added dropwise and stirring is continued for 18 hours. The reaction medium is poured into ice-water and extracted with ethyl acetate. The organic phase is separated out by settling of the phases, dried over magnesium sulfate and evaporated. 115 g of tert-butyl (3-bromophenyl)-N-methylcarbamate are obtained in a yield of 95%. stirring extracted with ethyl acetate The organic phase is separated out dried over magnesium sulfate evaporated
Source ID: ord-ba3433e1390b426396c07058c5da4ea4Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3.6 g (12.7 mmol) of tert-butyl (3-bromophenyl)-N-methylcarbamate, prepared in a manner analogous to Example 1b), are dissolved in 15 ml of dichloromethane. 5 ml of trifluoroacetic acid are added and the reaction mixture is stirred at ambient temperature for 1 hour. The reaction is halted by the addition of 50 ml of a saturated sodium hydrogencarbonate solution and then extraction is carried out with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated and then the residue is chromatographed on silica gel (heptane/ethyl acetate 50/50). 2.14 g of 3-bromo-N-methylaniline are obtained in the form of an oil. Yield=90%. extraction dried over sodium sulfate The solvents are evaporated the residue is chromatographed on silica gel (heptane/ethyl acetate 50/50)
Source ID: ord-68547b459c8d4acb9f3337b270c7cb90Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 128 g (470 mmol) of tert-butyl 3-bromophenylcarbamate in 800 mL of dimethylformamide, 19 g (475 mmol) of sodium hydride (60% in oil) are added portionwise and the reaction medium is stirred until the evolution of gas has ceased. 29.3 mL (470 mmol) of methyl iodide are added dropwise and stirring is continued for 18 hours. The reaction medium is poured into ice-cold water and extracted with ethyl acetate. The organic phase is separated out after settling of the phases, dried over magnesium sulfate and evaporated. 152.5 g (92%) of tert-butyl 3-bromophenyl-N-methylcarbamate are obtained. stirring The reaction medium is poured into ice-cold water extracted with ethyl acetate The organic phase is separated out dried over magnesium sulfate evaporated
Source ID: ord-86a40377e43d4f53830c5f2b55ca051dConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 129 g (475 mmol) of tert-butyl (3-bromophenyl)carbamate in 800 mL of dimethylformamide are added portionwise 19 g (475 mmol) of sodium hydride (60% in oil) and the reaction medium is stirred until the evolution of gas has ceased. 29 mL (470 mmol) of methyl iodide are added dropwise and stirring is continued for 18 hours. The reaction medium is poured into ice-cold water and extracted with ethyl acetate. The organic phase is separated out after settling of the phases, dried over magnesium sulfate, filtered and evaporated. 115 g (95%) of tert-butyl (3-bromophenyl)-N-methylcarbamate are obtained. stirring The reaction medium is poured into ice-cold water extracted with ethyl acetate The organic phase is separated out dried over magnesium sulfate filtered evaporated
Source ID: ord-b599c5a53c194c918e2b35c552be0eb2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 114 g (447 mmol) of tert-butyl (3-bromophenyl)carbamate in 800 ml of DMF are added portionwise 19 g (475 mmol) of sodium hydride (60% in oil) and the reaction medium is stirred until the evolution of gas has ceased. 29.3 ml (470 mmol) of methyl iodide are added dropwise and stirring is continued for 18 hours. The reaction medium is poured into ice-cold water and extracted with ethyl acetate. The organic phase is separated out after settling of the phases, dried over magnesium sulfate and evaporated. 115 g of tert-butyl (3-bromophenyl)-N-methylcarbamate are obtained in a yield of 95%. stirring The reaction medium is poured into ice-cold water extracted with ethyl acetate The organic phase is separated out dried over magnesium sulfate evaporated
Source ID: ord-9e174b4906214e0bad73be36a5c81fc0PubChem References
These sources are listed in the compound's public database record.
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