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Chemical Structure| 350490-15-2 Chemical Structure| 350490-15-2

Structure of 350490-15-2

Chemical Structure| 350490-15-2

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Product Details of [ 350490-15-2 ]

CAS No. :350490-15-2
Formula : C13H15BrO2
M.W : 283.16
SMILES Code : O=C(OC(C)(C)C)/C=C/C1=CC=C(Br)C=C1
MDL No. :MFCD24943187

Safety of [ 350490-15-2 ]

Application In Synthesis of [ 350490-15-2 ]

* 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.

  • Downstream synthetic route of [ 350490-15-2 ]

[ 350490-15-2 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 62327-21-3 ]
  • [ 1122-91-4 ]
  • [ 350490-15-2 ]
YieldReaction ConditionsOperation in experiment
Example 1; Preparation of 2-(4-bromophenyl)cyclopropanecarboxylic acid (4); Example 1a; Preparation of (E)-tert-butyl 3-(4-bromophenyl)acrylate (2); To a three-necked flask was charged with NaH (95percent, 2.6 g, 103 mmol) followed by Toluene (250 ml). The suspension was cooled to 5° C. and to the mixture was added the t-butyldimethylphosphonoacetate (95percent, 25.5 ml, 103 mmol) slowly keeping the temperature below 5° C. (very little exotherm observed and H2 gas generated), the resulting mixture was stirred at 5° C. for NLT20 min until no more H2 gas was generated). To the above mixture was then added the aldehyde (17.6 g, 94.2 mmol) and the resulting mixture was stirred at 10° C. for 2 hours and then at room temperature overnight. The reaction was monitored by HPLC until the starting material is consumed (<1.0 pa percent of aldehyde). The reaction mixture was poured into 400 ml of water and the organic layer was separated and washed with brine (400 ml), dried with Na2SO4 and concentrated to give an oil, which solidified upon standing to give crude product which was purified by crystallization from ethanol/water water (1:1, 30 mL/g) to give 25 g of product. 1H NMR (400 MHz, DMSO-d6) delta 1.47 (s, 9H), 6.53 (d, 1H, J=15.92), 7.50 (d, 1H, J=16.05), 7.57 (d, 2H, J=8.51), 7.63 (d, 2H, J=8.51). 13C NMR (100 MHz, DMSO-d6) delta 27.8, 79.8, 120.3, 123.0, 129.6, 131.3, 132.9, 141.6 164.6 with 4 peaks overlapping. A sample of the isolated product was purified by crystallization from ethanol/water (1:1, 30 mL/g). 1H NMR (400 MHz, DMSO-d6) delta 1.47 (s, 9H), 6.53 (d, 1H, J=15.92), 7.50 (d, 1H, J=16.05), 7.57 (d, 2H, J=8.51), 7.63 (d, 2H, J=8.51). 13C NMR (100 MHz, DMSO-d6) delta 27.8, 79.8, 120.3, 123.0, 129.6, 131.3, 132.9, 141.6 164.6 with 4 peaks overlapping.
  • 2
  • (Z)-5-(1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-1-en-1-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole [ No CAS ]
  • [ 101335-11-9 ]
  • [ 350490-15-2 ]
  • (E)-tert-butyl 3-(4-((E)-2-(2-chloro-4-fluorophenyl)-1-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)but-1-en-1-yl)phenyl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% To a 100 mL inerted reactor was added (Z)-5-(l,2-bis(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)but-l-en-l-yl)-l-(tetrahydro-2H-pyran-2-yl)-lH-indazole VI (2.89 g, 5.69 mmol), (E) -tert-butyl 3-(4-bromophenyl)acrylate (1.61 g, 5.69 mmol), tetrahydrofuran (8.7 mL), bis(triphenylphosphine)palladium(II) dichloride (0.040 g, 0.057 mmol), cesium carbonate (6.48 g, 19.9 mmol) and water (0.25 mL) at 15-25C. The reactor was inerted (5-10 min. of bubbling nitrogen through the reaction mixture) and the mixture heated to 60-65 C for at least 18 hrs. Upon completion based on HPLC analysis, the reaction mixture was cooled to 20C. 2-methyltetrahydrofuran (50 mL) and water (50 mL) were added and the mixture was stirred for 5-10 min. Stirring was stopped and the layers were allowed to separate for 5-10 min. The aqueous layer was removed, then <strong>[101335-11-9]2-chloro-4-fluoroiodobenzene</strong> (1.75 g, 6.83 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.040 g, 0.057 mmol) and 1.0 M potassium hydroxide (17 mL, 17 mmol) were charged to the reactor. The reactor was inerted (5-10 min. of bubbling nitrogen through the reaction mixture) and the mixture heated to 70 C for at least 18 hrs. Upon completion based on HPLC analysis, the reaction mixture was cooled to 20 C. The bottom aqueous layer was removed and the organic layer was washed with water (20 mL). The organics were dried with MgS04, filtered and concentrated under vacuum to give the crude product as dark brown oil. The crude product was purified by silica gel chromatography with a gradient of isopropyl acetate/heptane as eluent, then concentrated under vacuum to give (E)-tert-butyl 3-(4-((E)-2-(2-chloro-4- fluorophenyl)- 1 - ( 1 - (tetrahydro-2H-pyran-2-yl)- 1 H-indazol-5-yl)but- 1 -en- 1 - yl)phenyl)acrylate IX (2.35 g, 4.0 mmol, 70 % yield) as a light yellow oil. 1H NMR (300 MHz, DMSO-d6): delta 8.14 (s, IH), 7.75 (d, IH), 7.70 (s, IH), 7.42-7.32 (m, 5H), 7.28 (dt, IH), 7.14 (td, IH), 6.95 (s, IH), 6.92 (s, IH), 6.36 (d, IH), 5.86 (dd, IH), 3.90 (d, IH), 3.80-3.69 (m, IH), 2.47-2.31 (m, 3H), 2.11-1.93 (m, 2H), 1.85-1.67 (m, IH), 1.64-1.53 (m, 2H), 1.44 (s, 9H), 0.90 (t, 3H); LCMS: 587.2 [M+H]+.
 

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