No renderable structure data available
C1=CC(=CC=C1C(C(F)(F)F)(F)F)BrChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 1-bromo-4-(1,1,2,2,2-pentafluoroethyl)benzene |
|---|---|
| IUPAC Name | — |
| CAS Number | 206560-66-9 |
| Database ID | 54209708 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
1-bromo-4-(1,1,2,2,2-pentafluoroethyl)benzene (CAS 206560-66-9) 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 54209708
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-3a94ba2b5b5c44dab67c538a4226400aConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-3a94ba2b5b5c44dab67c538a4226400aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The requisite {cis-5-[4-(pentafluoroethyl)phenyl]tetrahydrofuran-2-yl}methanol was prepared via Suzuki reaction of (5-formylfuran-2-yl)boronic acid with 1-bromo-4-(pentafluoroethyl)benzene, followed by hydrogenation over palladium on carbon. 1-Bromo-4-(pentafluoroethyl)benzene was prepared according to the method of W. Lambert et al., PCT Int. Appl., 2011017513, Feb. 10, 2011.
Source ID: ord-d3e81d7f2a9241e2acb738957e629d14Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Pentafluoroethyl iodide (521 mg, 2.12 mmol) was condensed into a vial containing 1-bromo-4-iodobenzene (300 mg, 1.06 mmol), copper(0) powder (135 mg, 2.12 mmol), and DMSO (5 mL). The vial was then sealed and subjected to microwave irradiation at 150° C. for 60 min. GC-MS proved consumption of the starting material yielding both 1-bromo-4-pentafluoroethylbenzene and 1-iodo-4-pentafluoroethylbenzene intermediates. The mixture (1.06 mmol) was transferred to a 250 mL round bottom flask and 3-p-tolyl-1H-[1,2,4]triazole (169 mg, 1.06 mmol), Cs2CO3 (1.38 g, 4.24 mmol), CuI (202 mg, 1.06 mmol), 8-hydroxyquinoline (2 mg, 0.011 mmol), and DMF/H2O (12 mL; 10:1 solution) were added. The solution was stirred at reflux at 160° C. for 6 h. Upon completion, the cooled contents were poured into H2O and precipitation was allowed for 1 h. The precipitate was collected by vacuum filtration and dried overnight in a 45° C. vacuum oven. The crude 1-(4-pentafluoroethylphenyl)-3-p-tolyl-1H-[1,2,4]triazole intermediate was used in step 2 without further purification. condensed into The vial was then sealed irradiation at 150° C. for 60 min consumption of the starting material
Source ID: ord-c42c7b7ed16c44fc92ce6578d59b6c4cConditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Under argon in a microwave vial 2 g 1-bromo-4-iodobenzene, 3.3 g trimethyl(perfluoroethyl)silane, 493 mg potassium fluoride and 2 g copper iodide are suspended in 10 ml N,N-dimethylformamide. The mixture is heated for 12 hours at 80° C. Further 3.3 g trimethyl(perfluoroethyl)silane are added and heating is continued for 48 hours. Then the mixture is partitioned between 2 M ammonia and diethylether. The aqueous phase is twice extracted with diethylether. The combined organic phases are washed three times with water and dried with magnesium sulphate. The solvent is evaporated in vacuo (300 mbar, temperature of water bath 50° C.). The residue is chromatographed on silica gel (dichloromethane). heating Then the mixture is partitioned between 2 M ammonia and diethylether The aqueous phase is twice extracted with diethylether The combined organic phases are washed three times with water dried with magnesium sulphate The solvent is evaporated in vacuo (300 mbar, temperature of water bath 50° C.) The residue is chromatographed on silica gel (dichloromethane)
Source ID: ord-46f52acc79b14cd694f7e805bd7512fcConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Obtained by starting from (S)-5-(tert-butyldimethylsilyloxy)-4-iodo-2-isopropyl-7,7-dimethyl-5,6,7,8-tetrahydroquinoline-3-carbaldehyde and 1-bromo-4-(perfluoroethyl)benzene. Obtained
Source ID: ord-c1c3b16e23914d5199e3242eb326e606Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 1-(4-Pentafluoroethyl-phenyl)-3-p-tolyl-1H-[1,2,4]triazole. Pentafluoroethyl iodide (521 mg, 2.12 mmol) was condensed into a vial containing 1-bromo-4-iodobenzene (300 mg, 1.06 mmol), copper(0) powder (135 mg, 2.12 mmol), and DMSO (5 mL). The vial was then sealed and subjected to microwave irradiation at 150° C. for 60 min. GC/MS proved consumption of the starting material yielding both 1-bromo-4-pentafluoroethylbenzene and 1-iodo-4-pentafluoroethyl-benzene intermediates. The mixture (1.06 mmol), was transferred to a 250 mL round bottom flask and 3-p-tolyl-1H-[1,2,4]triazole (169 mg, 1.06 mmol), Cs2CO3 (1.38 g, 4.24 mmol), CuI (202 mg, 1.06 mmol), 8-hydroxyquinoline (2 mg, 0.011 mmol), and DMF/H2O (12 mL 10:1 solution) were added and the solution was refluxed at 160° C. for 6 h. Upon completion, the cooled contents were poured into H2O and precipitation was allowed for 1 h. The precipitate was collected by vacuum filtration and dried overnight in a 45° C. vacuum oven. The crude 1-(4-pentafluoroethylphenyl)-3-p-tolyl-1H-[1,2,4]triazole intermediate was used in step 2 without further purification. condensed into The vial was then sealed irradiation at 150° C. for 60 min consumption of the starting material
Source ID: ord-38be4f07905e4fd5b7238069dbf61a57Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A 1.5 M solution of n-butyllithium in tetrahydrofuran (0.57 mL) was added to a solution of 1-bromo-4-pentafluoroethylbenzene (180 mg, 0.65 mmol) in diethyl ether (1.0 mL) at −78° C., and the mixture was stirred for 20 minutes. Thereafter, trimethyl borate (101 mg, 3.28 mmol) was added and the mixture was stirred at −78° C. for 10 minutes and at room temperature for 30 minutes. 6 N aqueous hydrochloric acid (200 μL) was added to the reaction mixture, and the reaction was terminated. The mixture was then purified by silica gel column chromatography to give 4-pentafluoroethylphenylboronic acid as a white solid (111 mg, 71%). the mixture was stirred at −78° C. for 10 minutes and at room temperature for 30 minutes the reaction was terminated The mixture was then purified by silica gel column chromatography
Source ID: ord-2512b2e9ae4e4e0c8a3d042b3bc0d37cConditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 4-bromo-iodobenzene (500 mg, 1.77 mmol), trimethylsilylpentafluoroethane (679 mg, 3.53 mmol), copper iodide (672 mg, 3.53 mmol) and potassium fluoride (205 mg, 3.53 mmol) in N-methylpyrolidone (1.0 mL) was heated with stirring at 100° C. for three hours in a sealed reaction vessel. After cooling to room temperature, the reaction mixture was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to give 1-bromo-4-pentafluoroethylbenzene as a colorless liquid (253 mg, 52%). After cooling to room temperature the reaction mixture was purified by silica gel column chromatography (hexane:ethyl acetate=20:1)
Source ID: ord-9f3bb198234b457cb4a57fdafe605a95Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 1-(4-Pentafluoroethyl-phenyl)-3-p-tolyl-1H-[1,2,4]triazole. Pentafluoroethyl iodide (521 mg, 2.12 mmol) was condensed into a vial containing 1-bromo-4-iodobenzene (300 mg, 1.06 mmol), copper(0) powder (135 mg, 2.12 mmol), and DMSO (5 mL). The vial was then sealed and subjected to microwave irradiation at 150° C. for 60 min GC/MS proved consumption of the starting material yielding both 1-bromo-4-pentafluoroethylbenzene and 1-iodo-4-pentafluoroethyl-benzene intermediates. The mixture (1.06 mmol), was transferred to a 250 mL round bottom flask and 3-p-tolyl-1H-[1,2,4]triazole (169 mg, 1.06 mmol), Cs2CO3 (1.38 g, 4.24 mmol), CuI (202 mg, 1.06 mmol), 8-hydroxyquinoline (2 mg, 0.011 mmol), and DMF/H2O (12 mL 10:1 solution) were added and the solution was refluxed at 160° C. for 6 h. Upon completion, the cooled contents were poured into H2O and precipitation was allowed for 1 h. The precipitate was collected by vacuum filtration and dried overnight in a 45° C. vacuum oven. The crude 1-(4-pentafluoroethylphenyl)-3-p-tolyl-1H-[1,2,4]triazole intermediate was used in step 2 without further purification. condensed into The vial was then sealed irradiation at 150° C. for 60 min GC/MS consumption of the starting material
Source ID: ord-803eb43c05a24e6cb9d9a24ea091a270Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 1-(4-Pentafluoroethyl-phenyl)-3-p-tolyl-1H-[1,2,4]triazole. Pentafluoroethyl iodide (521 mg, 2.12 mmol) was condensed into a vial containing 1-bromo-4-iodobenzene (300 mg, 1.06 mmol), copper(0) powder (135 mg, 2.12 mmol), and DMSO (5 mL). The vial was then sealed and subjected to microwave irradiation at 150° C. for 60 min GC/MS proved consumption of the starting material yielding both 1-bromo-4-pentafluoroethylbenzene and 1-iodo-4-pentafluoroethyl-benzene intermediates. The mixture (1.06 mmol), was transferred to a 250 mL round bottom flask and 3-p-tolyl-1H-[1,2,4]triazole (169 mg, 1.06 mmol), Cs2CO3 (1.38 g, 4.24 mmol), CuI (202 mg, 1.06 mmol), 8-hydroxyquinoline (2 mg, 0.011 mmol), and DMF/H2O (12 mL 10:1 solution) were added and the solution was refluxed at 160° C. for 6 h. Upon completion, the cooled contents were poured into H2O and precipitation was allowed for 1 h. The precipitate was collected by vacuum filtration and dried overnight in a 45° C. vacuum oven. The crude 1-(4-pentafluoroethylphenyl)-3-p-tolyl-1H-[1,2,4]triazole intermediate was used in step 2 without further purification. condensed into The vial was then sealed irradiation at 150° C. for 60 min GC/MS consumption of the starting material
Source ID: ord-8f4e00a8dc7d49f881d17f4affaaafc6Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 1-(4-Pentafluoroethyl-phenyl)-3-p-tolyl-1H-[1,2,4]triazole. Pentafluoroethyl iodide (521 mg, 2.12 mmol) was condensed into a vial containing 1-bromo-4-iodobenzene (300 mg, 1.06 mmol), copper(0) powder (135 mg, 2.12 mmol), and DMSO (5 mL). The vial was then sealed and subjected to microwave irradiation at 150° C. for 60 min. GC-MS proved consumption of the starting material yielding both 1-bromo-4-pentafluoroethylbenzene and 1-iodo-4-pentafluoroethylbenzene intermediates. The mixture (1.06 mmol) was transferred to a 250 mL round bottom flask and 3-p-tolyl-1H-[1,2,4]triazole (169 mg, 1.06 mmol), Cs2CO3 (1.38 g, 4.24 mmol), CuI (202 mg, 1.06 mmol), 8-hydroxyquinoline (2 mg, 0.011 mmol), and DMF/H2O (12 mL; 10:1 solution) were added. The solution was stirred at reflux at 160° C. for 6 h. Upon completion, the cooled contents were poured into H2O and precipitation was allowed for 1 h. The precipitate was collected by vacuum filtration and dried overnight in a 45° C. vacuum oven. The crude 1-(4-pentafluoroethylphenyl)-3-p-tolyl-1H-[1,2,4]triazole intermediate was used in step 2 without further purification. condensed into The vial was then sealed irradiation at 150° C. for 60 min consumption of the starting material
Source ID: ord-74058091f43c428ab37a9c18fa85d12bPubChem References
These sources are listed in the compound's public database record.
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