Structure of 2368-53-8
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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. : | 2368-53-8 |
Formula : | C6HCl2F3 |
M.W : | 200.97 |
SMILES Code : | FC1=C(Cl)C(F)=C(Cl)C(F)=C1 |
MDL No. : | MFCD00012242 |
InChI Key : | UOGVNYNJSZHQCN-UHFFFAOYSA-N |
Pubchem ID : | 137563 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H227-H315-H319 |
Precautionary Statements: | P210-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P403+P235-P501 |
* 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 |
---|---|---|
94% | With calcium sulfate polyhydrate; calcium hydroxide; In diethylene glycol; at 120 - 140℃; | Diethylene glycol (390 g), calcium hydroxide (20 g) and calcium sulphate hydrate (34g) were added sequentially in a reaction vessel. The reaction mixture was heated to 120-140C. 3,5-Dichloro-2,4,6- trifluorobenzoic acid dissolved in diethylene glycol (1170 g) was added to the reaction mixture at 120-140C. The reaction mass was stirred for additional 1 to 2 hours. The 1,3 -dichloro-2,4,6-trifluorobenzene was recovered by distillation at 150- 180C. (0123) Yield: 94% (0124) Purity: 99.5% (by gas chromatography). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With chlorosulfonic acid; | Example A 3,5-Dichloro-2,4,6-trifluorophenylsulfonyl chloride 1,3-Dichloro-2,4,6-trifluorobenzene (5.0 g, 25 mmol) and chlorosulfonic acid (10.0 mL, 150 mmol) were mixed at ambient temperature under a nitrogen atmosphere and the reaction was heated at 80 C. for 24 h. The mixture was then allowed to cool to ambient temperature and was poured onto 12 g of crushed ice. The product was extracted with diethyl ether, dried over MgSO4, and the solvent was evaporated to produce 4.9 g of the title compound, which was used without further purification. MS(EI): 300 (30, M+), 298 (28), 263 (100), 199 (80). | |
With chlorosulfonic acid; | Example B 3,5-Dichloro-2,4,6-trifluorophenylsulfonyl Chloride. 1,3-Dichloro-2,4,6-trifluorobenzene (5.0 g, 25 mmol) and chlorosulfonic acid (10.0 ml, 150 mmol) were mixed at ambient temperature under a nitrogen atmosphere and the reaction was heated at 80 C. for 24 h. The mixture was then allowed to cool to ambient temperature and was poured onto 12 g of crushed ice. The product was extracted with diethyl ether, dried over MgSO4, and evaporated to produce 4.9 g of the title compound, which was used without further purification. MS (EI): 300 (30, M+), 298 (28), 263 (100), 199 (80). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With phosphinic acid; In ethanol; at 20℃; for 12h; | Step four, the three steps of the pure product or 10M after the product was concentrated, 10M hypophosphorous acid (or 8M, 12M, 15M, 20M, 30M range, is replaced or phosphorous acid or hypophosphorous acid is an acid salt / time phosphoric acid or a salt thereof) or 10M ethanol (or 20M, 30M, 40M, 50M, 60M range) into the reaction kettle and mixed well;Step five, kept at room temperature for 12 hours. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2987 g | With potassium iodide; at 20℃; for 12h;Large scale; | Step six, the 10M of KI (or 15M, 20M, 30M of KI, NaI, ICl, I2, KI3 or NaI3) into reactor, kept at room temperature for 12 hours;Step eight, after completion of the reaction was cooled to room temperature, washed with sodium nitrate acidic pH adjusted to 4-5 system, via at least once washed, acid-base refining and / or ethanol recrystallization process to obtain 2987g of product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With dipotassium hydrogenphosphate; palladium 10% on activated carbon; hydrogen; In water; at 140℃; under 11251.1 Torr; | l,3-Dichloro-2,4,6-trifluorobenzene (100 g), water (500 g), dipotassium hydrogen phosphate (260 g) and Palladium/carbon (10%; 2 g) were taken in a reaction vessel. Reaction vessel was flushed first with nitrogen and then with hydrogen. The reaction mixture was heated to 140C. Hydrogen gas was purged continuously into the reaction vessel at 140C and 15 kg/centimeter2 pressure. Progress of the reaction was monitored by gas chromatography. After completion of the reaction, reaction mass was cooled to 10-15C and excess hydrogen pressure was released. 1,3,5- trifluorobenzene was recovered from the reaction mass. The bottom mass containing Pd/ C was filtered, washed with fresh water and recycled in next batch. Yield: 85% (0126) Purity: 99.6% (gas chromatography). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With caesium carbonate; In N,N-dimethyl-formamide; at 130℃; for 3h;Inert atmosphere; | In an argon atmosphere,Add 25-1 (10.0g, 0.050mol) into a 500mL three-necked flask,3,6-Dimethoxycarbazole (11.4g, 0.050 mol)And cesium carbonate (57.5g, 0.13mol),Take 210mL of N,N-dimethylformamide (DMF) into the bottle,Warm up to 130C, stir and react for 3 hours,After cooling to room temperature, the reaction solution was added to 400 mL of saturated brine to settle,Filter, vacuum dry,The obtained solid was separated by a silica gel column to obtain product 25-2 (14.7 g, yield: 72%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With caesium carbonate; In N,N-dimethyl-formamide; at 130℃; for 3h;Inert atmosphere; | In an argon atmosphere,Add 25-1 (10.0g, 0.050mol) into a 500mL three-necked flask,N3,N3,N6,N6-tetrakis(4-tert-butylphenyl)-9H-carbazole-3,6-diamine (36.3g, 0.050mol)And cesium carbonate (57.5g, 0.13mol), take 250mL of N,N-dimethylformamide (DMF) into the bottle, heat to 130, stir and react for 3 hours, cool to room temperature, add 400mL saturated Settling in brine, filtering, and vacuum drying, the obtained solid was separated by silica gel column to obtain product 26-1 (29.5 g, yield: 65%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With caesium carbonate; In N,N-dimethyl-formamide; at 130℃; for 3h;Inert atmosphere; | In an argon atmosphere,Add 25-1 (10.0g, 0.050mol) into a 500mL three-necked flask,7H-Dibenzocarbazole (13.4g, 0.050 mol) and cesium carbonate (57.5g, 0.13mol),Take 230mL of N,N-dimethylformamide (DMF) into the bottle,Warm up to 130C, stir and react for 3 hours,After cooling to room temperature, the reaction solution was added to 400 mL of saturated brine to settle,Filter, vacuum dry,The obtained solid was separated by a silica gel column to obtain product 28-1 (14.8 g, yield: 66%). |
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