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Structure of 51368-55-9
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 51368-55-9 |
Formula : | C7H13BrO2 |
M.W : | 209.08 |
SMILES Code : | CC(C)(Br)C(OC(C)C)=O |
MDL No. : | MFCD00055235 |
InChI Key : | UNZJYKKJZGIFCG-UHFFFAOYSA-N |
Pubchem ID : | 2796293 |
GHS Pictogram: |
![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H225-H315-H319 |
Precautionary Statements: | P210-P233-P240-P241+P242+P243-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P403+P235-P501 |
Class: | 3 |
UN#: | 3272 |
Packing Group: | Ⅲ |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydrogencarbonate; In isopropyl alcohol; for 48h;Heating / reflux;Purification / work up; | Example 1 200 g of 4-chloro-4-hydroxybenzofenone, potassium bicarbonate (156 g), 360 g of isopropyl alpha-bromo isobutyrate and isopropanol (400 ml) were charged in a round bottom flask. The mixture was heated to reflux temperature for 48 hours, with stirring. After reaction completion, the reaction mixture was cooled at about 60C, and isopropanol (560 ml), acetone (240 ml), and a decolorizing agent (4.5 g of activated carbon) were added. The suspension was further cooled to about 40C, and stirring was continued for about 30 minutes. The suspension was filtered, and the solid was washed on the filter with a mixture of isopropanol and acetone. The filtrate was let to stand overnight at room temperature, and then stirred for additional 3-4 hours at 0-5C. Precipitated pure fenofibrate was filtered, washed on the filter with isopropanol and water. The compound was collected from the filter and dried at about 60 for 12 hours, to yield 220 g of pure fenofibrate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | In a 5L reactor configured to operate under reflux or rectification conditions,A mixture of 1108 g (5.28 mol) of isopropyl 2-bromo-2-methylpropanoate and 650 g (2.79 mol) of (4-chlorophenyl)(4-hydroxyphenyl)methanone at 145 ° C under nitrogen atmosphere heating,Mix thoroughly at the same time.Then add 448 g (3.24 mol) of potassium carbonate,The temperature of the reaction medium was raised to 155 °C.The reaction mixture was stirred at this temperature for 4 hours.During this time, the resulting aqueous phase was collected in a distiller.The temperature of the reaction medium was lowered to 145 ° C, and the internal pressure of the reactor was gradually lowered to remove excess bromination reactant by distillation.These conditions were maintained for about 2 hours during which time all of the distillate was collected in a reservoir. The temperature of the mixture was then lowered to 120 ° C, and the reactor was placed under normal pressure, and 1.95 L of propanol was added.The temperature of the mixture was then brought to about 80 ° C to 90 ° C and filtered under nitrogen pressure.The residual solid was washed on the filter with about 0.75 L of hot propanol.The filtrates kept at the same temperature were combined in a 5 L reactor.790 g (2.93 mol) of 45percent choline hydroxide were added stepwise, followed by the addition of 0.80 L of propanol.The reaction mixture was then boiled under normal pressure and the resulting distillate was collected until about 1.60 L of a propanol/water/isopropanol mixture was obtained.The mixture was filtered on a purification filter, and the filtrate was gradually cooled to about 10 ° C with stirring to crystallize the salt.The crystal salt separation was washed with 0.65 L of cold propanol on an aspirator and then dried in an oven under reduced pressure.800 g of the salt in the form of white crystals (i.e., the target product) were obtained (yield = 68percent). | |
67.5 - 70% | 2-[4-(4-Chlorobenzoyl)phenoxy]-2-methylpropanoic Acid Choline SaltA mixture of 1108 g (5.28 mol) of isopropyl 2-bromo-2-methylpropanoate and 650 g (2.79 mol) of (4-chlorophenyl)(4-hydroxyphenyl)methanone is heated at 145° C. under a nitrogen atmosphere, with thorough stirring, in a 5 l reactor equipped for operation under reflux or distillation. 448 g (3.24 mol) of potassium carbonate are then added and the temperature of the reaction medium is raised to 155° C. The reaction mixture is stirred at this temperature for 4 hours. During this period the aqueous phase produced is collected in the distillate. The temperature of the reaction medium is reduced to 145° C. and the internal pressure of the reactor is lowered gradually so as to remove the excess brominated reactant by distillation. These conditions are maintained for about 2 hours, during which time all the distillates are collected in a receiver. The temperature of the mixture is then reduced to 120° C. and, with the reactor at atmospheric pressure, 1.95 l of propanol are added. The mixture is then at a temperature of about 80-90° C. and is filtered under nitrogen pressure. The residual solid is rinsed on the filter with about 0.75 l of hot propanol. The filtrates, maintained at the same temperature, are combined in the 5 l reactor and 790 g (2.93 mol) of a 45percent aqueous solution of choline hydroxide are added gradually, followed by 0.80 l of propanol. The reaction mixture is then brought to the boil at atmospheric pressure and the distillate produced is collected until about 1.60 l of a propanol/water/isopropanol mixture have been obtained. The mixture is filtered on a clarifying filter and the filtrate is gradually cooled down to a temperature of about 10° C., with stirring, in order to crystallize the salt. The crystalline salt is separated off and washed with 0.65 l of cold propanol on an aspirator and then dried in an oven under reduced pressure.This gives 824 g of the expected salt in the form of white crystals (yield=70percent).The purity of the salt obtained is checked by HPLC, the assay being performed by the method described for fenofibrate in the European Pharmacopeia or the US Pharmacopeia. The fenofibric acid can be assayed by chromatography against a reference sample. The choline present in the salt is assayed by potentiometry.Analysis of the compound shows a purity in excess of 99.5percent and the absence of impurities in a proportion greater than 0.1percent.M.p.=213° C.; 2-[4-(4-Chlorobenzoyl)phenoxy]-2-methylpropanoic Acid Choline SaltA mixture of 100 g (0.43 mol) of (4-chlorophenyl)(4-hydroxyphenyl)-methanone and 148 g (0.82 mol) of methyl 2-bromo-2-methylpropanoate is prepared in a 1 l reactor maintained under a nitrogen atmosphere. The mixture is heated to 145° C., with thorough stirring, and 69 g (0.5 mol) of potassium carbonate are added. The reaction medium is maintained at 145° C. for 3 hours, with thorough stirring, during which time the water formed by the reaction is collected in the distillate. The pressure in the reactor is then gradually reduced in order to remove the excess brominated reactant by distillation. The mixture is then cooled to about 100° C. and 300 ml de n-propanol are added. The resulting mixture is stirred for 10 min at 90° C. and then filtered at this temperature to remove the insoluble mineral salts. The residual solid is rinsed with 100 ml of hot n-propanol, which is combined with the previous filtrates. The solution obtained is placed in the 1 l reactor under a nitrogen atmosphere and 121.5 g (0.45 mol) of a 45percent aqueous solution of choline hydroxide are added. The reaction mixture is stirred for 3 hours under gentle reflux of the solvent and about 240 ml of solvent are then distilled, 130 ml of n-propanol being added to the reactor. The reactor contents are subsequently filtered on a clarifying filter and then cooled slowly to about 15° C. The resulting suspension is filtered on an aspirator and the isolated solid is rinsed with 100 ml of cold n-propanol and then dried in a vacuum oven.This gives 122 g of the expected salt in the form of a white crystalline solid (yield=67.5percent).The purity of the salt obtained is greater than 99.5percent. |
Tags: 51368-55-9 synthesis path| 51368-55-9 SDS| 51368-55-9 COA| 51368-55-9 purity| 51368-55-9 application| 51368-55-9 NMR| 51368-55-9 COA| 51368-55-9 structure
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