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CAS No. : | 16220-95-4 | MDL No. : | MFCD12025214 |
Formula : | C9H9ClO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DLULLCMISBPNTK-UHFFFAOYSA-N |
M.W : | 184.62 | Pubchem ID : | 57362636 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* 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 N-Bromosuccinimide;dibenzoyl peroxide; In tetrachloromethane;Reflux; | A mixture of methyl 2-chloro-5-methylbenzoate (3.Og, 16.2 mmol), N- bromosuccinimide (3.O g, 17.0 mmol), and benzoyl peroxide (catalytic) in anhydrous carbon tetrachloride (50 mL) was stirred at reflux overnight. Dichloromethane (50 mL) was added after cooling to room temperature. The mixture was extracted with 1 N NaOH (2 x 100 mL). The organic layer was recovered, dried over MgSO4, filtered, evaporated, and dried in vacuo, affording methyl 5-(bromomethyl)-2-chlorobenzoate (4.06 g, 95% yield). The product was used without further purification. | |
With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; | General procedure: Corresponding 2-chloro-methylphenyl compounds (1 mmol) and PBO (0.1 mmol ) were dissolved in 5 mL CCl4, then NBS (1.1 mmol) was added slowly. The reaction was stirred at room temperature and monitored by TLC and cooled to room temperature upon completion of the reaction. The precipitated solid was filtrated and the filtrate was concentrated to give an oily liquid, which was directly subjected to a further reaction with Cs2CO3 (1.5 mmol) in 5 mL of CH3CN, and corresponding Schiff base (1 mmol) in dissolved CH3CN was added dropwise at room temperature. The solution was stirred at room temperature and monitored by TLC. Upon completion of the reaction, CH3CN was distilled off under reduced pressure and the residue was extracted CH2Cl2 (203 mL). Organic layer was dried over anhydrous Na2SO4, filtrated and concentrated under reduced pressure. The residue was purified by silica gel column to give the targeted compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(i) NBS, (PhCO)2O2, CCl4, (ii) /BRN= 783883/, NaOEt, EtOH; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2-Chlor-5-methylbenzoesaeure (VI), MeOH; | ||
Saeure (I), Me./H2SO4; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: NaOBr 2: (esterification) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: (i) NBS, (PhCO)2O2, CCl4, (ii) /BRN= 783883/, NaOEt, EtOH 2: aq. HCl |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | In methanol; dichloromethane; N,N-dimethyl-formamide; | Example 83 6-(2-CHLORO-5-METHYL-PHENYL)-N-(4-CHLORO-PHENYL)-[1,3,5]TRIAZINE-2,4-DIAMINE To a suspension of <strong>[6342-60-5]2-chloro-5-methyl-benzoic acid</strong> (3.0 g, 17.6 mmol) in dichloromethane (50 ml) was added a solution of oxalyl chloride in dichloromethane (2 M, 10 ml, 20 mmol) followed by N,N-dimethylformamide (5 drops). After stirring for 1 hour, methanol (20 ml) was added. After stirring for 3 hours, the mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate (200 ml) and saturated aqueous potassium carbonate solution (100 ml). The organic layer was concentrated under reduced pressure to provide methyl 2-chloro-5-methyl-benzoate (3.2 g, 100% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; copper(l) chloride; sodium nitrite In water at 0 - 5℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
sulfuric acid; for 5h;Reflux; | A mixture of <strong>[6342-60-5]2-chloro-5-methylbenzoic acid</strong> (4.0 g, 23.4 mmol) in methanol (50 niL) and a few drops of concentrated sulfuric acid were stirred at reflux for 5 hours. After cooling to room temperature, methanol was evaporated. The residue was dissolved in ethyl acetate (50 mL). The solution was extracted with saturated NaHCO3 (3 x 50 mL). The organic layer was dried over MgSO4, filtered, evaporated, and dried in vacuo, affording methyl 2-chloro-5-methylbenzoate (3.07g, 71% yield). The product was used without further purification. | |
With sulfuric acid; for 20h;Reflux; | A solution of 2- chloro-5-methylbenzoic acid (5g, 29.3 immol, 1 equiv.) in MeOH (60 mL) was added with concentrated H2S04 (1 mL), the mixture was refluxed for 20 h. Then cooled toroom temperature and concentrated to remove most of MeOH, the residue was diluted with water and extracted with CH2C12, dried over Na2SO4, concentrated and purified via FCC (Hexanes: EtOAc, 10:1) to give product methyl 2-chloro-5-methylbenzoate as grey solid. A solution of above obtained methyl 2-chloro-5-methylbenzoate in CC14 (60 mL) was added with NBS (13g, 2.5 equiv.) and benzoyl peroxide (5 mol%,0.4g), the mixture was stirred at reflux condition for 48 h, then cooled to room temperature and filtered, the filtrated was collected and concentrated. The cmde product was diluted with Et20 and filtered again, the filtrate was collect and concentrated, which was used for next step without purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / acetonitrile; tetrachloromethane / Reflux 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; sulfuric acid / toluene / Inert atmosphere 2.2: Inert atmosphere; Heating 2.3: 70 - 100 °C / Inert atmosphere 3.1: lithium hydroxide / methanol; water; tetrahydrofuran / 0.92 h / Heating 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / acetonitrile; tetrachloromethane / Reflux 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; sulfuric acid / toluene / Inert atmosphere 2.2: Inert atmosphere; Heating 2.3: 70 - 100 °C / Inert atmosphere 3.1: lithium hydroxide / methanol; water; tetrahydrofuran / 0.92 h / Heating 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / acetonitrile; tetrachloromethane / Reflux 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; sulfuric acid / toluene / Inert atmosphere 2.2: Inert atmosphere; Heating 2.3: 70 - 100 °C / Inert atmosphere 3.1: lithium hydroxide / methanol; water; tetrahydrofuran / 0.92 h / Heating 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 5.1: trifluoroacetic acid / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / acetonitrile; tetrachloromethane / Reflux 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; sulfuric acid / toluene / Inert atmosphere 2.2: Inert atmosphere; Heating 2.3: 70 - 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / acetonitrile; tetrachloromethane / Reflux 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; sulfuric acid / toluene / Inert atmosphere 2.2: Inert atmosphere; Heating 2.3: 70 - 100 °C / Inert atmosphere 3.1: lithium hydroxide / methanol; water; tetrahydrofuran / 0.92 h / Heating 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 5.1: trifluoroacetic acid / dichloromethane / 20 °C 6.1: sodium acetate / methanol; dichloromethane / 37 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / acetonitrile; tetrachloromethane / Reflux 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; sulfuric acid / toluene / Inert atmosphere 2.2: Inert atmosphere; Heating 2.3: 70 - 100 °C / Inert atmosphere 3.1: lithium hydroxide / methanol; water; tetrahydrofuran / 0.92 h / Heating 4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 5.1: trifluoroacetic acid / dichloromethane / 20 °C 6.1: sodium acetate / methanol; dichloromethane / 37 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / acetonitrile; tetrachloromethane / Reflux 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; sulfuric acid / toluene / Inert atmosphere 2.2: Inert atmosphere; Heating 2.3: 70 - 100 °C / Inert atmosphere 3.1: lithium hydroxide / methanol; water; tetrahydrofuran / 0.92 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane 2: caesium carbonate / acetonitrile / 20 °C 3: hydrazine hydrate / 0 - 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane 2: caesium carbonate / acetonitrile / 20 °C 3: hydrazine hydrate / 0 - 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane 2: caesium carbonate / acetonitrile / 20 °C 3: methanol / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane 2: caesium carbonate / acetonitrile / 20 °C 3: methanol / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane 2: caesium carbonate / acetonitrile / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane 2: caesium carbonate / acetonitrile / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 48 h / Reflux 1.2: 2 h / 50 °C 2.1: sodium dihydrogenphosphate; sodium chlorite / water; tetrahydrofuran; <i>tert</i>-butyl alcohol / 3 h / 20 °C 3.1: trichlorophosphate / 12 h / 90 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 48 h / Reflux 1.2: 2 h / 50 °C 2.1: sodium dihydrogenphosphate; sodium chlorite / water; tetrahydrofuran; <i>tert</i>-butyl alcohol / 3 h / 20 °C 3.1: trichlorophosphate / 12 h / 90 °C / Inert atmosphere 4.1: methanol; lithium hydroxide / 12 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 48 h / Reflux 1.2: 2 h / 50 °C 2.1: sodium dihydrogenphosphate; sodium chlorite / water; tetrahydrofuran; <i>tert</i>-butyl alcohol / 3 h / 20 °C 3.1: trichlorophosphate / 12 h / 90 °C / Inert atmosphere 4.1: methanol / 20 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 48 h / Reflux 1.2: 2 h / 50 °C 2.1: sodium dihydrogenphosphate; sodium chlorite / water; tetrahydrofuran; <i>tert</i>-butyl alcohol / 3 h / 20 °C 3.1: trichlorophosphate / 12 h / 90 °C / Inert atmosphere 4.1: methanol / 20 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 48 h / Reflux 1.2: 2 h / 50 °C 2.1: sodium dihydrogenphosphate; sodium chlorite / water; tetrahydrofuran; <i>tert</i>-butyl alcohol / 3 h / 20 °C 3.1: trichlorophosphate / 12 h / 90 °C / Inert atmosphere 4.1: methanol / 20 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 48 h / Reflux 1.2: 2 h / 50 °C 2.1: sodium dihydrogenphosphate; sodium chlorite / water; tetrahydrofuran; <i>tert</i>-butyl alcohol / 3 h / 20 °C 3.1: trichlorophosphate / 12 h / 90 °C / Inert atmosphere 4.1: ammonium hydroxide / dimethyl sulfoxide / 6 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 48 h / Reflux 1.2: 2 h / 50 °C 2.1: sodium dihydrogenphosphate; sodium chlorite / water; tetrahydrofuran; <i>tert</i>-butyl alcohol / 3 h / 20 °C 3.1: trichlorophosphate / 12 h / 90 °C / Inert atmosphere 4.1: methanol; lithium hydroxide / 12 h / 20 °C 5.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide; tetrahydrofuran / 4 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 48 h / Reflux 1.2: 2 h / 50 °C 2.1: sodium dihydrogenphosphate; sodium chlorite / water; tetrahydrofuran; <i>tert</i>-butyl alcohol / 3 h / 20 °C 3.1: trichlorophosphate / 12 h / 90 °C / Inert atmosphere 4.1: methanol; lithium hydroxide / 12 h / 20 °C 5.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 4 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: methyl 2-chloro-5-methylbenzoate With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 48h; Reflux; Stage #2: With silver nitrate In water; acetone at 50℃; for 2h; | A solution of 2- chloro-5-methylbenzoic acid (5g, 29.3 immol, 1 equiv.) in MeOH (60 mL) was added with concentrated H2S04 (1 mL), the mixture was refluxed for 20 h. Then cooled toroom temperature and concentrated to remove most of MeOH, the residue was diluted with water and extracted with CH2C12, dried over Na2SO4, concentrated and purified via FCC (Hexanes: EtOAc, 10:1) to give product methyl 2-chloro-5-methylbenzoate as grey solid. A solution of above obtained methyl 2-chloro-5-methylbenzoate in CC14 (60 mL) was added with NBS (13g, 2.5 equiv.) and benzoyl peroxide (5 mol%,0.4g), the mixture was stirred at reflux condition for 48 h, then cooled to room temperature and filtered, the filtrated was collected and concentrated. The cmde product was diluted with Et20 and filtered again, the filtrate was collect and concentrated, which was used for next step without purification.To a solution of crude product in acetone (50 mL) was added with AgNO3 (1 ig, 2.1equiv., in water 6 mL), the mixture was stirred at 50°C for 2h. Then filtered, thefiltrate was collect and concentrated to give crude product methyl 2-chloro-5-formylbenzoate. 1H-NMR (600 MHz, CDC13): ö 10.04 (s, 1H), 8.59 (s, 1H), 8.16- 8.15 (d, 1H), 7.62-7.60 (d, 1H), 4.00 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 48 h / Reflux 1.2: 2 h / 50 °C 2.1: sodium dihydrogenphosphate; sodium chlorite / water; tetrahydrofuran; <i>tert</i>-butyl alcohol / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With tetrakis(triphenylphosphine) palladium(0); potassium acetate; silver fluoride; CyJohnPhos In hexane at 140℃; for 20h; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / chloroform / Reflux; Inert atmosphere 2.1: lithium hydroxide / tetrahydrofuran / 20 h / 40 °C / Inert atmosphere 3.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 72 h / 20 °C / Inert atmosphere 4.1: triphenylphosphine; N-Bromosuccinimide / dichloromethane; acetonitrile / 2 h / 0 - 20 °C / Darkness; Inert atmosphere 4.2: 24 h / 50 °C / Darkness; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / chloroform / Reflux; Inert atmosphere 2: lithium hydroxide / tetrahydrofuran / 20 h / 40 °C / Inert atmosphere 3: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 4: triphenylphosphine; N-Bromosuccinimide / dichloromethane; acetonitrile / 2 h / 0 - 20 °C / Darkness; Inert atmosphere 5: silver nitrate / dichloromethane; acetonitrile / 24 h / 50 °C / Darkness; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / chloroform / Reflux; Inert atmosphere 2: lithium hydroxide / tetrahydrofuran / 20 h / 40 °C / Inert atmosphere 3: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 4: triphenylphosphine; N-Bromosuccinimide / dichloromethane; acetonitrile / 2 h / 0 - 20 °C / Darkness; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / chloroform / Reflux; Inert atmosphere 2: lithium hydroxide / tetrahydrofuran / 20 h / 40 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / chloroform / Reflux; Inert atmosphere 2: lithium hydroxide / tetrahydrofuran / 20 h / 40 °C / Inert atmosphere 3: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 72 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / chloroform / Reflux; Inert atmosphere 2: lithium hydroxide / tetrahydrofuran / 20 h / 40 °C / Inert atmosphere 3: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere |
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