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[ CAS No. 114776-15-7 ]

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Chemical Structure| 114776-15-7
Chemical Structure| 114776-15-7
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Product Details of [ 114776-15-7 ]

CAS No. :114776-15-7 MDL No. :MFCD04115715
Formula : C7H3ClFNO4 Boiling Point : 364.2°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :219.55 g/mol Pubchem ID :7210828
Synonyms :

Safety of [ 114776-15-7 ]

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
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Application In Synthesis of [ 114776-15-7 ]

  • Upstream synthesis route of [ 114776-15-7 ]
  • Downstream synthetic route of [ 114776-15-7 ]

[ 114776-15-7 ] Synthesis Path-Upstream   1~3

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YieldReaction ConditionsOperation in experiment
99% at 0 - 10℃; for 2 h; Compound 3-1 (9.3 g, 53.3 mmol) was dissolved in 100 ml of concentrated sulfuric acid,Nitric acid (3.5 g, 44.5 mmol) was added dropwise in an ice-water bath,The reaction was carried out at 0-10 ° C for 2 hours. After completion of the reaction, 0.5 L of ice water was added to the system,Extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated and purified by silica gel column.Compound 3-2 (11.7 g, 99.0percent) was obtained.
97.1%
Stage #1: With zirconium chloride; sulfuric acid; cobalt(II) chloride In ethanol; water at 25℃; for 1 h;
Stage #2: With nitric acid In ethanol; water at -5 - 8℃; for 1 h;
50 grams of concentrated sulfuric acid was charged into the reaction flask, 0.8 grams of the catalyst prepared in Example 1,10 g of 2-chloro-4-fluorobenzoic acid was added in portions and stirred at 25 ° C for 1 hour. The mixture was cooled to 0 ° C in an ice bath and 5 g of fuming nitric acid was added dropwise to control the reaction temperature at -5 to 8 ° C. 5 ~ 8 for 1 hour, the control 2-chloro-4-fluorobenzoic acid content of less than 0.5percent; the reaction was stirred slowly poured into 80 grams of crushed ice, filtered, the filter cake was rinsed with 30 grams of ice water , 65 blast drying, have white solid products12.0 g of 2-chloro-4-fluoro-5-nitrobenzoic acid was obtained in a yield of 97.1percent and a purity of 97.2percent. The weight content of the isomeric compound of formula (II) was 1.1percent.
58.1% With nitric acid In sulfuric acid Example 1
Preparation of 2-Chloro-4-fluoro-5-nitrobenzoic Acid
A solution of 2-chloro-4-fluorobenzoic acid (24.4 g, 0.142 mol) in 150 ml of concentrated sulfuric acid at 0° C. was treated dropwise with 90percent nitric acid (13.2 ml, 20 mol percent, 0.284 mol) over a 10 min. period at 10° C., stirred for 2.5 hours at 0 to 10° C., poured onto one liter of ice.
The white solid was filtered.
The filtercake was air-dried and recrystallized from ethyl acetate/heptane to afford the title compound as off-white needles. Yield: 18.0 g (58.1percent); identified by NMR spectral analysis.
Reference: [1] Patent: CN106866684, 2017, A, . Location in patent: Paragraph 0131-0132; 0204-0205
[2] Patent: CN106905161, 2017, A, . Location in patent: Paragraph 0014; 0015; 0016; 0017
[3] Farmaco, 2004, vol. 59, # 6, p. 463 - 471
[4] Synthesis, 1987, # 10, p. 883 - 887
[5] Patent: US2002/45550, 2002, A1,
[6] Patent: US6090753, 2000, A,
[7] Patent: US5700761, 1997, A,
[8] Patent: EP863142, 1998, A1,
[9] Patent: US6348628, 2002, B1, . Location in patent: Page column 60-61
[10] Patent: WO2007/95124, 2007, A2, . Location in patent: Page/Page column 54-55
[11] Patent: WO2008/28617, 2008, A1, . Location in patent: Page/Page column 58
[12] Patent: EP2511273, 2012, A1, . Location in patent: Page/Page column 50
[13] Patent: WO2012/140243, 2012, A1, . Location in patent: Page/Page column 69
[14] Patent: WO2013/106409, 2013, A1, . Location in patent: Page/Page column 56
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YieldReaction ConditionsOperation in experiment
82% at 70 - 110℃; for 3 - 6.45 h; EXAMPLE 3 Preparation of 2-chloro-4-fluoro-5-nitrobenzoic acid (according, to step (b)) Into a 250 ml reaction vessel 41.6 g of 96percent H2SO4 are loaded and 8.4 g of water added dropwise (to adjust the acid concentration to 80percent). The temperature of the acid is adjusted to 70°C and the portionwise addition of 10 g of purified 2-chloro-4-fluoro-5-nitrobenzotrichloride (titre by GC = 99.5percent) commenced. The temperature is then set to 100-110°C, observing the progressive formation of a white solid product dispersed in the mixture. The temperature is kept for 3 hours, then the reaction mixture cooled to 50°C and diluted with 100 g of water, and the product then extracted with 40 g of ethyl acetate at room temperature. The phases are separated and the organic solution washed with 46 g of water. Finally, the solvent is evaporated to give 7 g of the title product, as a white solid. Titre by HPLC = 94.5percent, molar yield 88percent. Melting point (°C): 148-151.EXAMPLE 4 Preparation of 2-chloro-4-fluoro-5-nitrobenzoic acid (according to step (b)) Into a 250 ml reaction vessel inside a 1 I glass equipped with mechanical means of stirring, thermometer, bubble condenser, thermostatically controlled oil heater, acid vapour water traps, 750 g of 96percent sulfuric acid are loaded and 75 g of deionised water added dropwise to dilute the acid to 85percent. The operation is completed over 1.5 hours, reaching a maximum temperature of 45°C. The acid is then heated to 80-90°C, and the portionwise addition of 302.6 g of crude 2-chloro-4-fluoro-5-nitrobenzotrichloride commenced. The production of HCl may be observed immediately, both in the reaction mixture (seen by foaming), and in the water absorption traps. The reaction is moderately exothermic, however, the portionwise addition continues in safety, avoiding the accumulation of gas with vigorous stirring. The temperature is kept between 80-100°C for the entire duration of the reaction, and for 3/4 of the duration, the reaction has the appearance of a solution, then the acid product begins to form a suspension despite the high temperature. Addition of the organic component is completed in 3 hours 45 minutes, divided into 15 minute periods with the addition of 20-30 g each. The reaction mixture is kept stirring at 100°C for a further 3 hours, until the reaction is complete. The gas absorbed in the traps (97.5 g) is an indication of the state of completion of the reaction. The reaction mixture is then cooled to 20°C, and then the product filtered to give 233 g of a creamy white, damp solid. It is then further purified by washing with water, filtration and drying to obtain 171.0 g of product. Hydrolysis molar yield: 82percent. Melting point (°C): 148-152.EXAMPLE 5 Preparation of 2-chloro-4-fluoro-5-nitrobenzoic acid (according to step (b)) Into a 250 ml reaction vessel 50 g of 96percent sulfuric acid are loaded then diluted to 80percent by the addition of 10 g of water. The mixture is then heated to 70°C and then the portionwise addition of 12 g of crude nitration product 2-chloro-4-fluoro-5-nitrobenzotrichloride (titre by GC = 98percent) commenced. The reaction mixture is heated to 100-110°C and kept at said temperature for 3 hours to promote the formation of the hydrolysis product. While cooling, it is diluted with the addition of 50 g of water and 50 g of ice, and the product extracted with 60 g of ethyl acetate. Following separation of the phases, the organic phase is washed with 60 g of water, and the ethyl acetate concentrated under reduced pressure. 10 g of heptane are then added and 8 g of title product isolated as a white solid. Titre by HPLC = 96.5percent, molar yield 91percent. Melting point (°C): 150-153.
Reference: [1] Patent: EP1853548, 2009, B1, . Location in patent: Page/Page column 6
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Reference: [1] Synthesis, 1987, # 10, p. 883 - 887
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