No renderable structure data available
BrC1C([H])=C([H])C(=C([H])C=1[H])C(N([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])=OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 4-BROMO-N-(1,1-DIMETHYLETHYL)BENZAMIDE |
|---|---|
| IUPAC Name | — |
| CAS Number | 42498-38-4 |
| Database ID | 603258 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
4-BROMO-N-(1,1-DIMETHYLETHYL)BENZAMIDE (CAS 42498-38-4) 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 603258
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-073504e499c94023b70761cf70dae5a1Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-5f113d02ead7405693d499236d086c70Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-2e126deff6f041668f33d64fc96690aaConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-073504e499c94023b70761cf70dae5a1Conditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 9,9 g of p-tert-butylaminocarbonylphenyl bromide is dissolved in 200 ml of dry tetrahydrofuran and cooled to -70° C. To the solution is added dropwise n-butyl lithium (5,3 g) in hexane and the mixture is stirred for one hour. 1-benzyl-5-[4-(4-fluorophenyl)-1-oxobutyl]-1H-imidazole (10,4 g) in 200 ml of tetrahydrofuran is added to the mixture at -70° C. and the mixture is allowed to warm to room temperature and stirring is continued over night. Saturated ammonium chloride is added to the mixture and the solution is extracted with ethyl acetate. Ethyl acetate fractions are combined and evaporated to dryness. to warm to room temperature stirring is continued over night the solution is extracted with ethyl acetate evaporated to dryness
Source ID: ord-3d543c7ead7d4e2db77bbcedf9e71a6cConditions: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 9,9 g of p-tert-butylaminocarbonylphenyl bromide is dissolved in 200 ml of dry tetrahydrofuran and cooled to -70° C. To the solution is added dropwise n-butyl lithium (5,3 g) in hexane and the mixture is stirred for one hour. 1-benzyl-5-[4-(4-fluorophenyl)-1-oxobutyl]-1H-imidazole (10,4 g) in 200 ml of tetrahydrofuran is added to the mixture at -70° C. and the mixture is allowed to warm to room temperature and stirring is continued over night. Saturated ammonium chloride is added to the mixture and the solution is extracted with ethyl acetate. Ethyl acetate fractions are combined and evaporated to dryness. to warm to room temperature stirring is continued over night the solution is extracted with ethyl acetate evaporated to dryness
Source ID: ord-3d543c7ead7d4e2db77bbcedf9e71a6cConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 6,95 g of N-tert-butyl-p-bromobenzamide is dissolved in 175 ml of tetrahydrofuran at -70° under nitrogen and 20.1 ml of n-butyllithium (2.7M) is added dropwise. After 30 min, a solution of 5.35 g of 4-(1-trityl-4-imidazolyl)-butanoic acid in 10 ml of tetrahydrofuran is added slowly. The reaction mixture is allowed to warm slowly to room temperature and 20 ml of an aqueous ammonium chloride solution is added. The organic layer is separated, dried over sodium sulfate and evaporated to yield 1-(p-N-tert-butylaminocarbonylphenyl)-4-(1-trityl-4-imidazolyl)-1-butanone The organic layer is separated dried over sodium sulfate evaporated
Source ID: ord-aff92d63a08445a1a2f661a94f2883eaConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 6,95 g of N-tert-butyl-p-bromobenzamide is dissolved in 175 ml of tetrahydrofuran at -70° under nitrogen and 20.1 ml of n-butyllithium (2.7M) is added dropwise. After 30 min, a solution of 5.35 g of 4-(1-trityl-4-imidazolyl)-butanoic acid in 10 ml of tetrahydrofuran is added slowly. The reaction mixture is allowed to warm slowly to room temperature and 20 ml of an aqueous ammonium chloride solution is added. The organic layer is separated, dried over sodium sulfate and evaporated to yield 1-(p-N-tert-butylaminocarbonylphenyl)-4-(1-trityl-4-imidazolyl)-1-butanone The organic layer is separated dried over sodium sulfate evaporated
Source ID: ord-aff92d63a08445a1a2f661a94f2883eaConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 25 mmoles of n-butyllithium in 10 ml of hexane is added dropwise to a solution of 3.19 g of N-tert-butyl 4-bromobenzamide in 250 ml of tetrahydrofuran at -70° under argon. After 30 min, a solution of 3.74 g of 3-(1-tritylimidazol-4-yl)propionaldehyde in 100 ml of tetrahydrofuran is added slowly. The reaction mixture is stirred at -70° for 30 min, allowed to warm to 25°, stirred at 25° for 2.5 h and quenched with excess saturated ammonium chloride solution. The aqueous layer is separated and extracted with methylene chloride (2×100 ml). The combined organic extracts are dried over sodium sulfate and evaporated. The residue is chromatographed on 220 g of silica with 5:1 ether:ethyl acetate to yield 4-[3-(4-tert-butylaminocarbonylphenyl)-3-hydroxyprop-1-yl]-1-tritylimidazole as an oil. IR (CH2Cl2): 1660 cm-1. to warm to 25° stirred at 25° for 2.5 h quenched with excess saturated ammonium chloride solution The aqueous layer is separated extracted with methylene chloride (2×100 ml) The combined organic extracts are dried over sodium sulfate evaporated The residue is chromatographed on 220 g of silica with 5:1 ether
Source ID: ord-950f77ea4a084ff7b276f4e360dca669Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 25 mmoles of n-butyllithium in 10 ml of hexane is added dropwise to a solution of 3.19 g of N-tert-butyl 4-bromobenzamide in 250 ml of tetrahydrofuran at -70° under argon. After 30 min, a solution of 3.74 g of 3-(1-tritylimidazol-4-yl)propionaldehyde in 100 ml of tetrahydrofuran is added slowly. The reaction mixture is stirred at -70° for 30 min, allowed to warm to 25°, stirred at 25° for 2.5 h and quenched with excess saturated ammonium chloride solution. The aqueous layer is separated and extracted with methylene chloride (2×100 ml). The combined organic extracts are dried over sodium sulfate and evaporated. The residue is chromatographed on 220 g of silica with 5:1 ether:ethyl acetate to yield 4-[3-(4-tert-butylaminocarbonylphenyl)-3-hydroxyprop-1-yl]-1-tritylimidazole as an oil. IR (CH2Cl2): 1660 cm-1. to warm to 25° stirred at 25° for 2.5 h quenched with excess saturated ammonium chloride solution The aqueous layer is separated extracted with methylene chloride (2×100 ml) The combined organic extracts are dried over sodium sulfate evaporated The residue is chromatographed on 220 g of silica with 5:1 ether
Source ID: ord-b1442f5fb2774e4a9b8b88696896133fConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 25 mmoles of n-butyllithium in 10 ml of hexane is added dropwise to a solution of 3.19 g of N-tert-butyl 4-bromobenzamide in 250 ml of tetrahydrofuran at -70° under argon. After 30 min, a solution of 3.74 g of 3-(1-tritylimidazol-4-yl)propionaldehyde in 100 ml of tetrahydrofuran is added slowly. The reaction mixture is stirred at -70° for 30 min, allowed to warm to 25°, stirred at 25° for 2.5 h and quenched with excess saturated ammonium chloride solution. The aqueous layer is separated and extracted with methylene chloride (2×100 ml). The combined organic extracts are dried over sodium sulfate and evaporated. The residue is chromatographed on 220 g of silica with 5:1 ether:ethyl acetate to yield 4-[3-(4-tert-butylaminocarbonylphenyl)-3-hydroxyprop-1-yl]-1-tritylimidazole as an oil. IR (CH2Cl2): 1660 cm-1. to warm to 25° stirred at 25° for 2.5 h quenched with excess saturated ammonium chloride solution The aqueous layer is separated extracted with methylene chloride (2×100 ml) The combined organic extracts are dried over sodium sulfate evaporated The residue is chromatographed on 220 g of silica with 5:1 ether
Source ID: ord-b1442f5fb2774e4a9b8b88696896133fConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 6.95 g of p-(tert-butylaminocarbonyl)-bromobenzene is dissolved in 175 ml of tetrahydrofuran at -70° under nitrogen and 20.1 ml of a solution of n-butyllithium (2.7M) in hexane is added dropwise. After reacting 30 min, a solution of 5.69 g of 4-(3-formyl-n-propyl)-1-trimethylsilylimidazole in 10 ml of tetrahydrofuran is added slowly. The reaction mixture is allowed to warm slowly to room temperature and 20 ml of ammonium chloride is added. The organic layer is separated, dried over sodium sulfate and evaporated to yield the title compound (b). The organic layer is separated dried over sodium sulfate evaporated
Source ID: ord-c90f12d3ba3d4c29b6ef22c6f07642cdPubChem References
These sources are listed in the compound's public database record.
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