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CAS No. : | 1483-55-2 | MDL No. : | MFCD03412187 |
Formula : | C8H3BrF3N | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ICEINTPQBJRYDE-UHFFFAOYSA-N |
M.W : | 250.02 | Pubchem ID : | 12223980 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | Example 108 Preparation of 2-methyl-5-phenyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1H-benzo[c]azepine, L-tartrate salt Step A: To a solution of the 2-bromo-5-trifluoromethyl-benzonitrile (2.6 g, 10.4 mmol) in toluene (20 mL) at -78 C. was added diisobutylaluminium hydride (21 mL, 21 mmol, 1.0 M in toluene) cooled to -78 C. by cannula. The solution was stirred at -78 to -50 C. for 2 hours. Water (5 mL) was added slowly to the reaction and the reaction was allowed to warm up to room temperature. The mixture was adjusted to pH 10 with NaOH. The product was extracted with dichloromethane, washed with saturated sodium bicarbonate and brine, dried over sodium sulfate and concentrated. The residue was purified by flash chromatography (hexanes/ether 90:10) to give the desired aldehyde (2.0 g, 76%) as a dark solid: 1H NMR (CDCl3, 300 MHz) delta 10.38 (s, 1H), 8.18 (s, 1H), 7.68 (d, J=8.7 Hz, 1H), 7.54 (d, J=8.7 Hz, 1H). | |
To a solution of <strong>[1483-55-2]2-bromo-5-(trifluoromethyl)benzonitrile</strong> (10.0 g, 40 mmol) in dichloromethane (100 mL) was dropwise added a 1.0 M solution of diisobutylaluminum hydride in hexane (48 mL). The resulting solution was stirred under nitrogen at ambient temperature for 1 h and was then diluted by addition of ether (100 mL). After cooling in an ice bath, a 3 N solution of HCl was carefully added, and the mixture was vigorously stirred at ambient temperature for 15 min. The organic layer was washed with brine, dried (MgSO4) and evaporated. The resulting oil was purified by flash chromatography (5% EtOAc/hexane) affording 5 g of 2-bromo-5-trifluoromethylbenzaldehyde. 1H NMR (CDCl3) delta 10.39 (s, 1H), 8.18 (d, J=2 Hz, 1H), 7.82 (d, J=8.8 Hz, 1H), 7.70 (dd, J=8.5 Hz, 2 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Specific examples of the trifluoromethylbenzonitrile include 2-trifluoromethylbenzonitrile, 3-trifluoromethylbenzonitrile, 4-trifluoromethylbenzonitrile, 2-bromo-5-trifluoromethylbenzonitrile, 2-chloro-5-trifluoromethylbenzonitrile, 2-fluoro-5-trifluoromethylbenzonitrile, 4-iodo-2-trifluoromethylbenzonitrile, 4-iodo-3-trifluoromethylbenzonitrile, 2-methoxy-5-trifluoromethylbenzonitrile, ... | ||
Specific examples of the trifluoromethylbenzonitrile include 2-trifluoromethylbenzonitrile, 8-trifluoromethylbenzonitrile, 4-trifluoromethylbenzonitrile, 2-bromo-5-trifluoromethylbenzonitrile, 2-chloro 5-trifluoromethylbenzonitrile, 2-fluoro-5-trifluoromethylbenzonitrile, 4-iodo-2-trifluoromethylbenzonitrile, 4-iodo 3-trifluoromethylbenzonitrile, 2-methoxy-5-trifluoromethylbenzonitrile, 3-methoxy-4-trifluoromethylbenzonitrile, ... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With diisobutylaluminium hydride; In hydrogenchloride; dichloromethane; | (a) 2-(8-Phenyloctyl)-5-trifluoromethyl benzaldehyde To a solution of <strong>[1483-55-2]2-bromo-5-trifluoromethyl benzonitrile</strong> (20.16 mmoles) in methylene chloride (50 ml), under argon at room temperature, was added diisobutylaluminum hydride (25 mmoles, 25 ml hexane) dropwise and the resulting solution was stirred for 30 minutes. The reaction mixture was diluted with ether (50 ml), cooled in ice and quenched by the careful addition of hydrochloric acid (50 ml, 3N). The ice bath was removed and the mixture was stirred vigorously for 15 minutes. The organic layer was washed with brine (50 ml), treated with magnesium sulfate-charcoal and evaporated. The resulting oil was purified by distillation to give 2-bromo-5-trifluoromethyl benzaldehyde, bp 50-55 C. at 0.05 mm Hq. | |
With diisobutylaluminium hydride; In hydrogenchloride; dichloromethane; | (a) 2-(8-Phenyloctyl)-5-trifluoromethyl benzaldehyde To a solution of <strong>[1483-55-2]2-bromo-5-trifluoromethyl benzonitrile</strong> (20.16 mmoles) in methylene chloride (50 ml), under argon at room temperature, was added diisobutylaluminum hydride (25 mmoles, 25 ml hexane) dropwise and the resulting solution was stirred for 30 minutes. The reaction mixture was diluted with ether (50 ml), cooled in ice and quenched by the careful addition of hydrochloric acid (50 ml, 3 N). The ice bath was removed and the mixture was stirred vigorously for 15 minutes. The organic layer was washed with brine (50 ml), treated with magnesium sulfate-charcoal and evaporated. The resulting oil was purified by distillation to give 2-bromo-5-trifluoromethyl benzaldehyde, bp 50-55 C. at 0.05 mm Hg. | |
With diisobutylaluminium hydride; In hydrogenchloride; dichloromethane; | (a) 2-(8-Phenyloctyl)-5-trifluoromethyl benzaldehyde To a solution of <strong>[1483-55-2]2-bromo-5-trifluoromethyl benzonitrile</strong> (20.16 mmoles) in methylene chloride (50 ml), under argon at room temperature, was added diisobutylaluminum hydride (25 mmoles, 25 ml hexane) dropwise and the resulting solution was stirred for 30 minutes. The reaction mixture was diluted with ether (50 ml), cooled in ice and quenched by the careful addition of hydrochloric acid (50 ml, 3N). The ice bath was removed and the mixture was stirred vigorously for 15 minutes. The organic layer was washed with brine (50 ml), treated with magnesium sulfate-charcoal and evaporated. The resulting oil was purified by distillation to give 2-bromo-5-trifluoromethyl benzaldehyde, bp 50-55 C. at 0.05 mm Hg. |
With diisobutylaluminium hydride; In hydrogenchloride; dichloromethane; | (a) 2-(8-Phenyloctyl)-5-trifluoromethyl benzaldehyde To a solution of <strong>[1483-55-2]2-bromo-5-trifluoromethyl benzonitrile</strong> (20.16 mmoles) in methylene chloride (50 ml), under argon at room temperature, was added diisobutylaluminum hydride (25 mmoles, 25 ml hexane) dropwise and the resulting solution was stirred for 30 minutes. The reaction mixture was diluted with ether (50 ml), cooled in ice and quenched by the careful addition of hydrochloric acid (50 ml, 3N). The ice bath was removed and the mixture was stirred vigorously for 15 minutes. The organic layer was washed with brine (50 ml), treated with magnesium sulfate-charcoal and evaporated. The resulting oil was purified by distillation to give 2-bromo-5-trifluoromethyl benzaldehyde, bp 50-55 C. at 0.05 mm Hg. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In hydrogenchloride; dichloromethane; | (a) 2-(8-Phenyloctyl)-5-trifluoromethyl benzaldehyde To a solution of <strong>[1483-55-2]2-bromo-5-trifluoromethyl benzonitrile</strong> (20.16 mmoles) in methylene chloride (50 ml), under argon at room temperature, was added diisobutyl-aluminum hydride (25 mmoles, 25 ml hexane) dropwise and the resulting solution was stirred for 30 minutes. The reaction mixture was diluted with ether (50 ml), cooled in ice and quenched by the careful addition of hydrochloric acid (50 ml, 3N). The ice bath was removed and the mixture was stirred vigorously for 15 minutes. The organic layer was washed with brine (50 ml), treated with magnesium sulfate-charcoal and evaporated. The resulting oil was purified by distillation to give 2-bromo-5-trifluoromethyl benzaldehyde, bp 50-55 C. at 0.05 mm Hg. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
15% | With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 85℃; for 1h; | Example 192: 4-Chloro-6-(2-piperazin-l-yl-5-trifluoromethyl-benzylamino)-2H- phthalazin-1-one; 4-(2-Cyano-4-tfluoromethyl-phenyl)-piperazine-l-carboxylic acid tert-butyl ester; A mixture of Boc-piperazine (573mg, (3.08 mmol), 2-bromo-5- trifluoromethylbenzonitrile (700mg, 2.80mmol), Pd2(dba)3 (256mg, 0.28 mmol), xantphos (486mg, 0.84mmol), sodium t-butoxide (660mg, 7.0mmol) in degassed anhydrous dioxane (1OmL) was heated at 85C for Ih. The mixture was allowed to cool and filtered through celite. The filtrate was concentrated and purified by chromatography (EtOAc/hexanes) to yield the title compound (150mg, 15%). m/z (M+ 1) 356.37. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 95℃; for 16h; | A mixture of 4-chloro-N-[2-(3-hydroxy-propoxy)-6-methyl-phenyl]-N- methyl-3-(4A5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-benzamide (206 mg, 0.45 mmol), <strong>[1483-55-2]2-bromo-5-(trifluoromethyl)-benzonitrile</strong> (75 mg, 0.3 mmol), Pd(PPh3)4 (34.7 mg, 0.03 mmol), Na2CO3 (190.8 mg, 1.8 mmol) in dioxane/water (9/1 , 1.5 ml_), was heated at 95 0C for approximately 16 hrs after degassing of the solvent with a stream of nitrogen. The reaction was allowed to cool to room temperature. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was further washed with brine and dried with MgSO4. The filtrate was evaporated and the residue purified by preparative TLC [eluent: 40% acetone in hexane] to afford 4-chloro-3-(2- cyano^-trifluoromethyl-phenyO-N-^^S-hydroxy-propoxyJ-theta-methyl-phenyll-N-methyl- benzamide 10-1 (120 mg). MS [M+H]+: 502.9; tR= 8.15 min. (method 2) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(l) iodide; triethylamine;tetrakis(triphenylphosphine) palladium(0); at 80℃; for 4h;Inert atmosphere; | <strong>[1483-55-2]2-Bromo-5-trifluoromethyl-benzonitrile</strong> (10Og, 0.40 mol) was dissolved in triethylamine (600 mL), and the solution was sparged with Ar for 20 min. CuI(I) (2.5 g, 0.013 mol), Pd(PPh3)4 (450 mg, 0.38 mmol), and TM S -acetylene (50 g, 0.51 mol) were added, and the reaction was stirred at 80 0C for 1 h. A small amount of precipitate developed, and additional CuI(I) (1 g), Pd(PPh3)4 (1.5 g), and TMS-acetylene (15 mL) were added. The reaction was stirred at 80 0C for 3 h more. The reaction mixture was diluted with 1.5 L of hexanes and filtered through celite. The solvents were removed to give tan crystals. These crystals were dissolved in methanol (250 mL) and potassium carbonate (Ig) was added. The mixture was stirred at RT for 2 h. The reaction mixture was then partitioned between ether (500 mL) and water (150 mL). The organic layer was washed with water until it was no longer basic by pH paper (about 10 times). The organic layer was washed with brine, dried over sodium sulfate, and concentrated then purified via silica gel chromatography using EtOAc in hexanes (2-10%). The 2-ethynyl-5-trifluoromethyl-benzonitrile was collected as a tan solid (62.5 g). H1 NMR (CDCl3): £(ppm) 7.93-7.92 (m, 1 H), 7.84-7.80 (m, 1 H), 7.76-7.74 (d, 1 H), 3.64 (s, 1 H). |
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