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Chemical Structure| 844648-19-7 Chemical Structure| 844648-19-7

Structure of 844648-19-7

Chemical Structure| 844648-19-7

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Product Details of [ 844648-19-7 ]

CAS No. :844648-19-7
Formula : C9H8F2O3
M.W : 202.16
SMILES Code : O=C(O)CCOC1=CC(F)=CC(F)=C1
MDL No. :MFCD17170974

Safety of [ 844648-19-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H312-H332
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501

Application In Synthesis of [ 844648-19-7 ]

* 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.

  • Upstream synthesis route of [ 844648-19-7 ]

[ 844648-19-7 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 844648-19-7 ]
  • [ 844648-22-2 ]
YieldReaction ConditionsOperation in experiment
86% at 50℃; for 1.5 h; At a temperature of 50 0C, 3-(3,5-difluorophenoxy)propanoic acid (20.0 g, 99 mol) was dissolved portion-wise into 60 ml of concentrated sulfuric acid. The resulting yellow-green solution was stirred for 1.5 hours at 50 0C, cooled to room temperature, and poured on ice water (800 ml). After a period of 1 hour, the colourless precipitate was isolated by filtration and washed with water. The title compound was dried over phosphorous pentaoxide: 15.69 g of a colourless solid, 86 percent yield
84% at 10 - 50℃; Large scale 345 kg of concentrated sulfuric acid was introduced into the reactor A,After cooling to 10 ° C, 142 kg of 3- (3,5-difluorophenoxy) propanoic acid was added dropwise.50 After stirring,After the reaction was completed, the reaction mixture was cooled to 20 ° C.1421 kg of purified water was charged into the reactor B,0 & gt; C.The reaction product of the reactor A was slowly dropped into the reactor B while maintaining the temperature at 10 ° C or lower, and 1890 kg of dichloromethane was added and stirred.After separating the organic layer,1421 kg of purified water was added and the pH was adjusted to 7.5 using a 5percent sodium carbonate aqueous solution (14 kg of sodium carbonate + 284 kg of purified water).The organic layer was separated, concentrated in vacuo at 40 & lt; 0 &483 kg of heptane was added and stirred.After filtration, it was vacuum-dried at 40 DEG C,5,7-difluorochroman-4-one (109 kg, 84percent).
73%
Stage #1: With thionyl chloride In toluene for 1.5 h; Heating / reflux
Stage #2: With trifluorormethanesulfonic acid In chloroform at -65 - 20℃; for 2 h;
Stage #3: With sodium hydroxide In chloroform; water
To a solution of 3-(3,5-difluorophenoxy)-propionic acid (1.11 g, 5.49 mol) in toluene (10 mL) was added thionyl chloride (2.0 mL, 27 mmol). The solution was heated at reflux for 1.5 h, then was concentrated in vacuo. The residue was dissolved in CHCl3 (10 mL), cooled to -65° C., and treated dropwise with trifluoromethanesulfonic acid (0.73 mL, 8.2 mmol). The mixture was allowed to warm to room temperature with stirring over 2 h. After the addition of H2O, the layers were separated. The organic layer was washed with 1 N NaOH, then dried over MgSO4, filtered, concentrated, and purified by flash chromatography (hexanes/EtOAc) to provide the title compound (0.73 g, 73percent). TLC (silica, 50percent EtOAc/hexanes): Rf=0.43. 1H NMR (400 MHz, CDCl3): 6.52-6.47 (m, 2H), 4.54 (t, J=6.4 Hz, 2H), 2.80 (t, J=6.4 Hz, 2H).
References: [1] Patent: WO2008/151927, 2008, A2, . Location in patent: Page/Page column 61.
[2] Patent: KR2018/11830, 2018, A, . Location in patent: Paragraph 0061; 0076; 0077.
[3] Patent: US2005/38032, 2005, A1, . Location in patent: Page/Page column 31.
 

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