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Chemical Structure| 1372195-69-1 Chemical Structure| 1372195-69-1

Structure of 1372195-69-1

Chemical Structure| 1372195-69-1

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Product Details of [ 1372195-69-1 ]

CAS No. :1372195-69-1
Formula : C12H17BrO3S
M.W : 321.23
SMILES Code : O=S(CCCOC1=CC(C)=C(Br)C(C)=C1)(C)=O
MDL No. :MFCD26393754

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Application In Synthesis of [ 1372195-69-1 ]

* 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 [ 1372195-69-1 ]

[ 1372195-69-1 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 263400-88-0 ]
  • [ 7463-51-6 ]
  • [ 1372195-69-1 ]
YieldReaction ConditionsOperation in experiment
85% With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 24h;Inert atmosphere; To a solution of 4-bromo-3,5-dimethylphenol (2.01g, lOmmol) and 3 -(methyl sulfonyl)propyl 4-methylbenzenesulfonate (3.5 lg, 12.0mmol) in N,N-dimethylformamide (20mL) was added potassium carbonate (1.80g, 13.0mmol), and the mixture was stirred at 90 C for 24 hr under nitrogen atmosphere. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with 1M aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (ethyl acetate : hexane=40:60-80:20), and the obtained crystals were recrystallized from heptane-ethyl acetate to give a colorless crystals product 25 (2.73g, yield 85%).
67% With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 24h; Weighing 4-bromo-3,5(dimethyl)phenol (2.0g, 10mmol), YZ-1 (2.92g, 10mmol), potassium carbonate (2.76g, 20mmol), dissolved in 20ml N,N-dimethyl formamide, in the reaction system 90 C stirring in oil bath 24 hours. In the reaction system by adding 150 ml ethyl acetate dilution, water sequentially, saturated salt water washing, anhydrous sulfuric acid nano dry, filtered, concentrated to obtain crude products, rapid column chromatography purification (petroleum ether: ethyl acetate: dichloromethane = 1:1:1), to obtain the product 12e (2.15g), yield 67%.
With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 46h;Product distribution / selectivity; Example 9Synthesis of 2-bromo-l, 3-dimethyl-5- [3- (methylsulfonyl) propoxy] benzene; [0420][0421]4-Bromo-3, 5-dimethylphenol (40.00 g) , 3- (methylsulfonyl) propyl 4-methylbenzenesulfonate (72.71 g) and potassium carbonate (35.75 g) were added toN, N-dimethylformamide (400 mL) , and the mixture was stirred. The mixture was heated to 70C, stirred for 46 hr, and cooled to 5C. Water (200 mL) was added dropwise at 10C or below, seed crystal (60 mg) was added, and water (400 mL) was continuously added. After stirring for 2 hr, the precipitated crystals were collected by filtration, washed with water (400 mL) and dried to give the title compound (63.08 g) .XH NMR (300 MHz, CDC13) : delta 2.28-2.36 (m, 2H) , 2.38 (s, 6H) , 2.93-2.97 (m, 3H) , 3.20-3.26 (m, 2H) , 4.07 (t, J=5.8 Hz, 2H) , 6.63 (s, 2H) , 7.26 (s, 1H) .
With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 18h; Step C: 2-bromo- 1,3 -dimethyl-5 -(3 -(methylsulfonyl)propoxy)benzene (34-3)To a solution of compound 34-2 (32.1 g, 110 mmol) in DMF (300 mL) was added 4-bromo-3,5- dimethylphenol (20.1 g, 100 mmol), and K2C03 (16.5 g, 120 mmol). The resulting mixture was stirred at 100 C for 18 hours. Then water was added and the mixture was extracted with ethyl acetate (150 mL x 3). The combined organic layers were washed with brine, dried and concentrated to give a residue. The residue was purified by chromatography on silica gel(petroleum ether:ethyl acetate = 3/1) to give compound 34-3. MS (ESI) m1z(M+H):32 1.0/323.0.
With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 18h; To a solution of compound 34-2 (32.1 g, 110 mmol) in DMF (300 mL) was added 4-bromo-3,5-dimethylphenol (20.1 g, 100 mmol), and K2C03 (16.5 g, 120 mmol). The resulting mixture wasstirred at 100 C for 18 hours. Then water was added and the mixture was extracted with ethylacetate (150 mL x 3). The combined organic layers were washed with brine, dried andconcentrated to give a residue. The residue was purified by chromatography on silica gel15 (petroleum ether:ethyl acetate= 3/1) to give compound 34-3. MS (ESI) m/z(M+Hf:321.0/323.0.

  • 2
  • [ 443776-76-9 ]
  • [ 1372195-69-1 ]
  • [ 1000413-85-3 ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In tetrahydrofuran; water; for 16h;Inert atmosphere; Reflux; Step D: (2?,6?-dimethyl-4?-(3 -(methylsulfonyl)propoxy)- [1,1 ?-biphenyll -3 -yl)methanol (34-4)To a mixture of compound 34-3 (10 g, 31.1 mmol), (3-(4,4,5 ,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)phenyl)methanol (7.64 g, 32.6 mmol) and K3P04 (15.7 g, 77.9 mmol) in a co-solvent ofTHF/H20 (120/30 mL) was added Pd(dppf)2C12 (1.27 g, 1.56 mmol) under a nitrogen atmosphere. The resulting mixture was heated to reflux for 16 h. After cooling to room temperature, the mixture was filtered through a Celite pad and the filtrate was extracted with ethyl acetate twice. The combined organic layers were washed with water, dried andconcentrated in vacuo to obtain a residue, which was purified by column chromatography on silica gel (petroleum ether:ethyl acetate = 3/1) to give compound 34-4. MS (ESI) m1z(M+H):349.1.
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In tetrahydrofuran; water; for 16h;Inert atmosphere; Reflux; To a mixture of compound 34-3 (10 g, 31.1 mmol), (3-( 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-20 2-yl)phenyl)methanol (7.64 g, 32.6 mmol) and K3P04 (15.7 g, 77.9 mmol) in a co-solvent ofTHF/H20 (120/ 30 mL) was added Pd(dppf)2Ch (1.27 g, 1.56 mmol) under a nitrogenatmosphere. The resulting mixture was heated to reflux for 16 h. After cooling to roomtemperature, the mixture was filtered through a Celite TM pad and the filtrate was extracted withethyl acetate twice. The combined organic layers were washed with water, dried and25 concentrated in vacuo to obtain a residue, which was purified by column chromatography onsilica gel (petroleum ether:ethyl acetate= 3/1) to give compound 34-4. MS (ESI) m/z(M+Hf:349.1.
 

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