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Chemical Structure| 474554-34-2 Chemical Structure| 474554-34-2

Structure of 474554-34-2

Chemical Structure| 474554-34-2

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Product Details of [ 474554-34-2 ]

CAS No. :474554-34-2
Formula : C10H11Br2FO2
M.W : 342.00
SMILES Code : CCOC1=C(F)C(Br)=C(Br)C=C1OCC
MDL No. :MFCD22050880
InChI Key :SCCURTWFEJWBPF-UHFFFAOYSA-N
Pubchem ID :11709889

Safety of [ 474554-34-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 474554-34-2 ]

* 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 [ 474554-34-2 ]

[ 474554-34-2 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 474554-34-2 ]
  • [ 544-92-3 ]
  • [ 474554-45-5 ]
YieldReaction ConditionsOperation in experiment
55% With 1,3-dimethyl-2-imidazolidinone; at 130 - 140℃; for 21.0h; [Preparation Example 1] Production of 4.5-diethoxy-3-fluorophthalonitrile A mixture of 1,2-dibromo-4,5-diethoxy-3-fluorobenzene (137.0 g, 0.401 mol, content: 81%), copper cyanide (107.5 g, 1.200 mol) and 1,3-dimethyl-2-imidazolidinone (600 mL) was subjected to nitrogen substitution under reduced pressure, then heated and stirred at 130C for 17 hours and at 140C for four hours under nitrogen atmosphere. After the reaction mixture was cooled to room temperature, N,N-dimethylformamide (600 mL), toluene (1.2 L) and concentrated aqueous ammonia (1.2 L) were added thereto, and the layers were separated. The resultant organic layer was washed by adding N,N-dimethylformamide (411 mL) and concentrated aqueous ammonia (800 mL). The organic layer was further washed sequentially with a 25% aqueous solution of ethylenediamine (1.2 L), 1N hydrochloric acid (1.2 L), and water (1.2 L), filtered through activated carbon, and concentrated at 50C under reduced pressure to give a yellow sherbet-like residue. The residue was dissolved by adding toluene (100 mL) and n-heptane (100 mL) and heating to 60C, and the solution was cooled to 10C or lower by stirring, to precipitate crystals which were then filtered. The resultant crystals were dissolved by adding toluene (50 mL) and n-heptane (50 mL) and heating to 90C, and the solution was stirred at room temperature to precipitate crystals. After cooling to 10C or lower, the crystals were filtered, and dried at 50C under reduced pressure to give 51.5 g of the title compound (yield: 55%) as white crystals.
In DMF (N,N-dimethyl-formamide); at 150℃; for 3.0h; After dissolving the 1,2-dibromo-4,5-diethoxy-3-fluorobenzene (480 g) in dimethylformamide (1400 ml), copper cyanide (345 g) was added and the mixture was stirred at 150C for 3 hours. Saturated aqueous ammonia was added to the reaction mixture, and then the mixture was stirred overnight and extraction was performed with toluene. The organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (513 g) as white crystals.1H-NMR(CDCl3)δ(ppm) 1.38(3H,t,J=7.0Hz), 1.50(3H,t,J=7.0Hz), 4.16(2H,q,J=7.0Hz), 4.27(2H,q,J=7.0Hz), 7.04(1H,s).
  • 2
  • [ 226555-35-7 ]
  • [ 474554-34-2 ]
YieldReaction ConditionsOperation in experiment
With bromine; sodium acetate; In acetic acid; at 0 - 70℃; for 14.0h; After dissolving the 1,2-diethoxy-3-fluorobenzene (269 g) in acetic acid (2000 ml), sodium acetate (294.5 g) was added. A solution of bromine (178 ml) in 150 ml of acetic acid was gradually added thereto dropwise while cooling on ice. After stirring overnight at room temperature, the mixture was stirred at 70C for 14 hours. The reaction mixture was poured into ice water, potassium carbonate was added to adjust the pH to 7, and extraction was performed with ether. The organic layer was dried over anhydrous magnesium sulfate to yield the title compound (480 g) as a brown oil.1H-NMR(CDCl3)δ(ppm) 1.35(3H,t,J=7.0Hz), 1.43(3H,t,J=7.0Hz), 4.04(2H,q,J=7.0Hz), 4.11(2H,q,J=7.0Hz), 6.98(1H,s).
  • 3
  • [ 474554-34-2 ]
  • 3,4-dibromo-6-ethoxy-2-fluorophenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% After dissolving 1,2-dibromo-3-fluoro-4,5-diethoxybenzene (5 g, 14.5 ml) in dichloromethane (70 ml), aluminum chloride (3.9 g, 29.3 mmol) was added while stirring on ice. The mixture was stirred at room temperature for 2 hours 30 minutes, 1 N hydrochloric acid (70 ml) was added and extraction was performed with ethyl acetate (70 ml x 2) and then after washing the combined organic layers with brine (50 ml) and drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to obtain the title compound (4.31 g, 94%).1H-NMR(CDCl3)δ(ppm) 1.45(3H,t,J=7.0Hz), 4.10(2H,q,J=7.0Hz), 5.49(1H,s), 6.95(1H,s).
  • 4
  • 5-bromo-1,2-diethoxy-3-fluorobenzene [ No CAS ]
  • [ 474554-34-2 ]
YieldReaction ConditionsOperation in experiment
100% With bromine; sodium acetate; In acetic acid; at 20 - 50℃; for 1.5h; To a solution of 5-bromo-1,2-diethoxy-3-fluorobenzene (40.0 g, 0.15 mol) in acetic acid (200 mL), sodium acetate (16.2 g, 0.20 mol) and bromine (31.6 g, 0.20 mol) were added sequentially at room temperature, and the mixture was stirred at 50C for 1.5 hours. The reaction mixture was cooled to room temperature, and a saturated aqueous solution of sodium thiosulfate (400 mL) and water (400 mL) were added sequentially. The mixture was extracted once with heptane (800 mL) and three times with heptane (400 mL). The organic layer was washed sequentially with water (400 mL), once with a 2 N aqueous solution of sodium hydroxide (200 mL), once with a 2 N aqueous solution of sodium hydroxide (100 mL), and water (400 mL), then dried over anhydrous magnesium sulfate. The solvent was distilled off from the organic layer under reduced pressure and the residue was filtered. The filtrate was then purified by silica gel column chromatography (hexane, ethyl acetate) to give 52.0 g of the title compound (yield: quant.).
 

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