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CAS No. : | 73502-03-1 | MDL No. : | MFCD11045607 |
Formula : | C10H12O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SEVHDRXGLLXUQE-UHFFFAOYSA-N |
M.W : | 180.20 | Pubchem ID : | 11745224 |
Synonyms : |
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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 |
---|---|---|
98% | With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 3 h; Heating / reflux | Intermediate 12:Compound 11 (4.4 g, 24.2 mmol) was dissolved in carbon tetrachloride (80 ml_) and N-bromosuccinimide (4.48 g, 24.2 mmol) and benzoyl peroxide (276 mg, 1.13 mmol) were added. The reaction mixture was stirred at reflux for 3 hours and then solids were filtered and washed with ether. The combined organic layers were washed with water, dried over sodium sulfate, and concentrated to provide the desired product 12 (6.1 g, 98percent). Mass calculated for formula C10H11 BrO3 259.10, observed LCMS m/z 260 (M+H), NMR (H1); 4.50(2H,CH2- Br) 3.73(3H, -OCH3),3.88(3 H, CO2-CH3),6.86-7.5(m,3H,Aromatic) |
98% | With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 3 h; Reflux | Part B: Compound 2 (4.4 g, 24.2 mmol) was dissolved in carbon tetrachloride (80 ml_) and N-bromosuccinimide (4.48 g, 24.2 mmol) and benzoyl peroxide (276 mg, 1.13 mmol) were added. The reaction mixture was stirred at reflux for 3 hours and then solids were filtered and washed with ether. The combined organic layers were washed with water, dried over sodium sulfate, and concentrated to provide the desired product 3 (6.1 g, 98percent). |
98% | With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 2 h; Heating / reflux | A mixture of ( 5.68 g, 31.1 mmol), NBS(6.74 g, 37.9 mmol), AIBN (259 mg,1.58 mmol) in carbon tetrachloride was refluxed for 2 hr. The reaction mixture was cooled at room temperature and the solid was filtrated under vacuum. The filtrate was concentrated in vacuo to obtain (75) (8.01 g, >98 percent ) as an oil without purification. |
98% | With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 3 h; Heating / reflux | Part B: Compound 301 (4.4 g, 24.2 mmol) was dissolved in carbon tetrachloride (80 mL) and N-bromosuccinimide (4.48 g, 24.2 mmol) and benzoyl peroxide (276 mg, 1.13 mmol) were added. The reaction mixture was stirred at reflux for 3 hours and then solids were filtered and washed with ether. The combined organic layers were washed with water, dried over sodium sulfate, and concentrated to provide the desired product 302 (6.1 g, 98percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With magnesium 1.) ether, reflux, 0.5 h, 2.) ether, reflux, 2 h; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) LiBr, K, NH3, t-BuOH, 3.) LiOH*H2O / 1) THF, -78 deg C, 10 min; 2) THF, -78 deg C, 30 min, -78 deg C --> rt, 30 min; 3) MeOH, H2O, reflux, 19 h 2: Bu3SnH, AIBN / benzene / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) LiBr, K, NH3, t-BuOH, 3.) LiOH*H2O / 1) THF, -78 deg C, 10 min; 2) THF, -78 deg C, 30 min, -78 deg C --> rt, 30 min; 3) MeOH, H2O, reflux, 19 h 2: Bu3SnH, AIBN / benzene / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 1.) Mg / 1.) ether, reflux, 0.5 h, 2.) ether, reflux, 2 h 2: 35 percent / TiCl3, LiAlH4 / 1,2-dimethoxy-ethane / 16 h / Heating 3: 1.) BBr3, 2.) 2N NaOH / 1.) CH2Cl2, RT, 4 h, 2.) CH2Cl2, MeOH |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) Mg / 1.) ether, reflux, 0.5 h, 2.) ether, reflux, 2 h 2: 35 percent / TiCl3, LiAlH4 / 1,2-dimethoxy-ethane / 16 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With caesium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 110℃; for 16h; | Compound 1008A (20g, 81.61 mmol), 1008B (13.36 mL, 97.93 mmol),Pd(dppf)CI2 (1.0g, 1.36 mmol), dioxane (350 mL), water (50 mL), and Cs2CO3(22. 5g, 163 mmol) were stirred at 110 C (oil bath) under nitrogen for 16hours. After cooling, the solid was removed by filtration. The solution wasconcentrated and purified by SGC (Hexane/EtOAc, 10:1) to give 1008C |
80% | With caesium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 110℃; for 16h; | Intermediate 11 :Methyl 2-bromo-5-methoxy benzoate (20.0 g, 81.61 mmol), tri methyl bo roxine (13.36 ml_, 97.93 mmol), Pd(dppf)CI2 (1.0 g, 1.36 mmol), dioxane (350 ml_), water (50 ml_), and Cs2CO3 (22.5 g, 163 mmol) were stirred at 11OC (oil bath) under nitrogen for 16 hours. After cooling, the solid was removed by filtration. The solution was concentrated and purified by SGC (10:1 EtOAc/hexanes) to give 11 (12.1 g, 80%). Mass calculated for formula C10H12NO3 , 180.20, observed LCMS m/z 181.20 (M+H).NMR (H1); 2.35(3H,CH3) 3.73(3H, - OCH3),3.88(3 H, CO2-CH3),6.86-7.5(m,3H,Aromatic) |
80% | With caesium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 110℃; for 16h;Inert atmosphere; | Example 1; Part A: Compound 1 (20.0 g, 81.61 mmol), trimethylboroxine (13.36 ml_, 97.93 mmol),Pd(dppf)CI2 (1.0 g, 1.36 mmol), dioxane (350 ml_), water (50 ml_), and cesium carbonate (22.5 g, 163 mmol) were stirred at 110 0C (oil bath) under nitrogen for 16 hours. After cooling, the solid was removed by filtration. The solution was concentrated and purified by sgc (10:1 EtOAc/hexanes) to give 2 (12.1 g,80%). |
80% | With caesium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 110℃; for 16h; | Part A: Compound 300 (20.0 g, 81.61 mmol), trimethylboroxine (13.36 mL, 97.93 mmol), Pd(dppf)CI2 (1.0 g, 1.36 mmol), dioxane (350 mL), water (50 mL), and cesium carbonate (22.5 g, 163 mmol) were stirred at 110 0C (oil bath) under nitrogen for 16 hours. After cooling, the solid was removed by filtration. The solution was concentrated and purified by sgc (10:1 EtOAc/hexanes) to give 301 (12.1 g, 80%). |
80% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; at 110℃; for 16h;Inert atmosphere; | Compound 1 (20.0 g, 81.61 mmol), trimethylboroxine (13.36 mL, 97.93 mmol), Pd(dppf)Cl2 (1.0 g, 1.36 mmol),dioxane (350 mL), water (50 mL), and cesium carbonate (22.5 g, 163 mmol) were stirred at 110 C (oil bath) undernitrogen for 16 hours. After cooling, the solid was removed by filtration. The solution was concentrated and purified bysgc (10:1 EtOAc/hexanes) to give 2 (12.1 g, 80%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 3.0h;Heating / reflux; | Intermediate 12:Compound 11 (4.4 g, 24.2 mmol) was dissolved in carbon tetrachloride (80 ml_) and N-bromosuccinimide (4.48 g, 24.2 mmol) and benzoyl peroxide (276 mg, 1.13 mmol) were added. The reaction mixture was stirred at reflux for 3 hours and then solids were filtered and washed with ether. The combined organic layers were washed with water, dried over sodium sulfate, and concentrated to provide the desired product 12 (6.1 g, 98%). Mass calculated for formula C10H11 BrO3 259.10, observed LCMS m/z 260 (M+H), NMR (H1); 4.50(2H,CH2- Br) 3.73(3H, -OCH3),3.88(3 H, CO2-CH3),6.86-7.5(m,3H,Aromatic) |
98% | With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 3.0h;Reflux; | Part B: Compound 2 (4.4 g, 24.2 mmol) was dissolved in carbon tetrachloride (80 ml_) and N-bromosuccinimide (4.48 g, 24.2 mmol) and benzoyl peroxide (276 mg, 1.13 mmol) were added. The reaction mixture was stirred at reflux for 3 hours and then solids were filtered and washed with ether. The combined organic layers were washed with water, dried over sodium sulfate, and concentrated to provide the desired product 3 (6.1 g, 98%). |
> 98% | With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 2.0h;Heating / reflux; | A mixture of ( 5.68 g, 31.1 mmol), NBS(6.74 g, 37.9 mmol), AIBN (259 mg,1.58 mmol) in carbon tetrachloride was refluxed for 2 hr. The reaction mixture was cooled at room temperature and the solid was filtrated under vacuum. The filtrate was concentrated in vacuo to obtain (75) (8.01 g, >98 % ) as an oil without purification. |
98% | With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 3.0h;Heating / reflux; | Part B: Compound 301 (4.4 g, 24.2 mmol) was dissolved in carbon tetrachloride (80 mL) and N-bromosuccinimide (4.48 g, 24.2 mmol) and benzoyl peroxide (276 mg, 1.13 mmol) were added. The reaction mixture was stirred at reflux for 3 hours and then solids were filtered and washed with ether. The combined organic layers were washed with water, dried over sodium sulfate, and concentrated to provide the desired product 302 (6.1 g, 98%). |
98% | With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 3.0h;Reflux; | Compound 2 (4.4 g, 24.2 mmol) was dissolved in carbon tetrachloride (80 mL) and N-bromosuccinimide (4.48g, 24.2 mmol) and benzoyl peroxide (276 mg, 1.13 mmol) were added. The reaction mixture was stirred at reflux for 3hours and then solids were filtered and washed with ether. The combined organic layers were washed with water, driedover sodium sulfate, and concentrated to provide the desired product 3 (6.1 g, 98%). |
With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; at 77.0℃; for 3.0h; | Intermediate 1-3Preparation of 2-(3-bromo-2-methylphenyl)-6-methoxyisoindolin-1-one Step 1 A suspension of methyl 5-methoxy-2-methylbenzoate (1.00 g, 5.55 mmol), N-bromosuccinimide (1.037 g, 5.83 mmol) and benzoyl peroxide (81 mg, 0.333 mmol) in tetrachloromethane (10 mL) was heated at 77 C. for 3 h. The mixture was diluted with DCM, washed with NaHCO3 (aq), dried and concentrated to provide crude methyl 2-(bromomethyl)-5-methoxybenzoate as a light yellow solid (1.435 g), used without further purification. 1H NMR (400 MHz, chloroform-d) delta 7.48 (1H, d, J=2.64 Hz), 7.37 (1H, d, J=8.36 Hz), 7.02 (1H, dd, J=8.58, 2.86 Hz), 4.93 (2H, s), 3.95 (3H, s), 3.85 (3H, s). | |
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In chloroform; for 21.0h;Reflux; | To a solution of methyl o-methylbenzoate (1.00 equiv) in CHCl3 (2-5 mL per mmol of methyl o-methylbenzoate) or CCl4 (5 mL per mmol of methyl o-methylbenzoate) was added NBS(1.10-2.20 equiv) and AIBN (0.02-0.04 equiv). The reaction was refluxed for 2-22 h before being cooled to rt. The solvent was then removed in vacuo (CHCl3 solvent) or via distillation (CCl4 solvent) within a fumehood to afford the desired brominated compound. CAUTION: CHCl3 and especially CCl4 are extremely toxic and carcinogenic and thus must be handled cautiously with gloves and within a fumehood appropriately ventilated. | |
With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; at 80.0℃; for 1.0h; | Methyl 5-methoxy-2-methylbenzoate(4.8 g, 26.0 mmol) is dissolved in CCl4 (100 mL), followed by adding NBS (5.1 g, 28.6 mmol), (PhCO2)2 (315 mg, 1.30 mmol), and the reaction mixture reacts with a reflux for 1 hr at 80 C, then the reaction mixture is cooled down to room temperature, and poured into ice water(150 mL), and extracted with dichloromethane (100 mL * 3), the organic layer is combined, dried with anhydrous Na2SO4, filtered and rotated to remove the solvent, so as to obtain a yellow oily matter of 7.5 g, that is methyl 2-(bromomethyl)-5-methoxybenzoate, which is used in the following reaction without purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With bis(triphenylphosphine)nickel(II) chloride In N,N-dimethyl-formamide at 55℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate; In N,N-dimethyl-formamide; at 0 - 20℃; | 5-Methoxy-2-methylbenzoic acid (3.95 g, 26.0 mmol) is dissolved in DMF(30 mL), followed by adding Cs2CO3 (21.21 g, 65.0 mmol), and dripping CH3I (4.1 mL, 65.0 mmol) at 0 C in 10 min, then the temperature is increased to room temperature, and the reaction mixture reacts overnight, then filtered with sillceousearth. Then the filtrate is poured into water (100 mL), the mixture is extracted with ethyl acetate (60 mL * 2), and subsequently the organic layer is combined and washed with saturated salt solution (60 mL * 2), dried with anhydrous Na2SO4 and filtered, rotated to dryness, so as to obtain a yellow oily matter of 4.80 g, that is methyl 5-methoxy-2-methylbenzoate, which is directly used for the next reaction. Spectrum is: 1H NMR (400 MHz, CDCl3) delta: 7.46(d, J =2.8 Hz,1H), 7.16(d, J = 8.4 Hz,1H), 6.97(dd, J = 8.4 Hz, 2.8 Hz,1H), 3.91(s, 3H), 3.83(s, 3H), 2.53(s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sulfuric acid / water / 2.5 h / 160 °C 1.2: 2.5 h / 190 °C 2.1: potassium hydroxide / water / 16 h / Reflux 3.1: sulfuric acid / 16 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 14h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 18h; | To a solution of benzoic acid (1.0 equiv) in DMF (3.8 mL per mmol of benzoic acid) was added CH3I (3.0-6.0 equiv) and K2CO3 (2.5-5.0 equiv). The solution was heated to 70 C for 17-18 h. After being cooled to rt, the reaction mixture was quenched by addition of H2O. The organics were extracted with EtOAc, combined, dried over MgSO4 and concentrated in vacuo within a fumehood to afford the desired ester. CAUTION: CH3I is toxic and carcinogenic and thus must be handled cautiously with gloves and within a fumehood appropriately ventilated. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: palladium on activated charcoal; hydrogen / ethyl acetate / 20 °C 2.1: sulfuric acid; sodium nitrite / water / 0.5 h / 0 °C 2.2: 0.5 h / Reflux 3.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3 h / 72 °C 2.1: potassium carbonate / acetone / 4 h / Reflux 3.1: potassium hydroxide / water; methanol / 4 h / 40 °C 4.1: trifluoroacetic anhydride / dichloromethane / 0.5 h / 20 °C 4.2: 0.5 h 5.1: boron tribromide / dichloromethane / -20 °C / Inert atmosphere 6.1: potassium carbonate / acetone / 6 h / Reflux; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3 h / 72 °C 2.1: potassium carbonate / acetone / 4 h / Reflux 3.1: potassium hydroxide / water; methanol / 4 h / 40 °C 4.1: trifluoroacetic anhydride / dichloromethane / 0.5 h / 20 °C 4.2: 0.5 h 5.1: boron tribromide / dichloromethane / -20 °C / Inert atmosphere 6.1: potassium carbonate / acetone / 6 h / Reflux; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3 h / 72 °C 2.1: potassium carbonate / acetone / 4 h / Reflux 3.1: potassium hydroxide / water; methanol / 4 h / 40 °C 4.1: trifluoroacetic anhydride / dichloromethane / 0.5 h / 20 °C 4.2: 0.5 h 5.1: boron tribromide / dichloromethane / -20 °C / Inert atmosphere 6.1: potassium carbonate / acetone / 6 h / Reflux; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3 h / 72 °C 2.1: potassium carbonate / acetone / 4 h / Reflux 3.1: potassium hydroxide / water; methanol / 4 h / 40 °C 4.1: trifluoroacetic anhydride / dichloromethane / 0.5 h / 20 °C 4.2: 0.5 h 5.1: boron tribromide / dichloromethane / -20 °C / Inert atmosphere 6.1: potassium carbonate / acetone / 6 h / Reflux; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3 h / 72 °C 2.1: potassium carbonate / acetone / 4 h / Reflux 3.1: potassium hydroxide / water; methanol / 4 h / 40 °C 4.1: trifluoroacetic anhydride / dichloromethane / 0.5 h / 20 °C 4.2: 0.5 h 5.1: boron tribromide / dichloromethane / -20 °C / Inert atmosphere 6.1: potassium carbonate / acetone / 6 h / Reflux; Inert atmosphere 7.1: caesium carbonate; XPhos; palladium diacetate / 1,4-dioxane; <i>tert</i>-butyl alcohol / 3 h / 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3 h / 72 °C 2.1: potassium carbonate / acetone / 4 h / Reflux 3.1: potassium hydroxide / water; methanol / 4 h / 40 °C 4.1: trifluoroacetic anhydride / dichloromethane / 0.5 h / 20 °C 4.2: 0.5 h 5.1: boron tribromide / dichloromethane / -20 °C / Inert atmosphere 6.1: potassium carbonate / acetone / 6 h / Reflux; Inert atmosphere 7.1: caesium carbonate; XPhos; palladium diacetate / 1,4-dioxane; <i>tert</i>-butyl alcohol / 3 h / 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3 h / 72 °C 2.1: potassium carbonate / acetone / 4 h / Reflux 3.1: potassium hydroxide / water; methanol / 4 h / 40 °C 4.1: trifluoroacetic anhydride / dichloromethane / 0.5 h / 20 °C 4.2: 0.5 h 5.1: boron tribromide / dichloromethane / -20 °C / Inert atmosphere 6.1: potassium carbonate / acetone / 6 h / Reflux; Inert atmosphere 7.1: caesium carbonate; XPhos; palladium diacetate / 1,4-dioxane; <i>tert</i>-butyl alcohol / 3 h / 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3 h / 72 °C 2.1: potassium carbonate / acetone / 4 h / Reflux 3.1: potassium hydroxide / water; methanol / 4 h / 40 °C 4.1: trifluoroacetic anhydride / dichloromethane / 0.5 h / 20 °C 4.2: 0.5 h 5.1: boron tribromide / dichloromethane / -20 °C / Inert atmosphere 6.1: potassium carbonate / N,N-dimethyl-formamide / 6 h / Reflux; Inert atmosphere 7.1: caesium carbonate; XPhos; palladium diacetate / 1,4-dioxane; <i>tert</i>-butyl alcohol / 3 h / 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3 h / 72 °C 2.1: potassium carbonate / acetone / 4 h / Reflux 3.1: potassium hydroxide / water; methanol / 4 h / 40 °C 4.1: trifluoroacetic anhydride / dichloromethane / 0.5 h / 20 °C 4.2: 0.5 h 5.1: boron tribromide / dichloromethane / -20 °C / Inert atmosphere 6.1: potassium carbonate / N,N-dimethyl-formamide / 6 h / Reflux; Inert atmosphere 7.1: caesium carbonate; XPhos; palladium diacetate / 1,4-dioxane; <i>tert</i>-butyl alcohol / 4 h / 110 °C / Inert atmosphere 8.1: toluene-4-sulfonic acid / water; methanol / Reflux 9.1: 0.67 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3 h / 72 °C 2.1: potassium carbonate / acetone / 4 h / Reflux 3.1: potassium hydroxide / water; methanol / 4 h / 40 °C 4.1: trifluoroacetic anhydride / dichloromethane / 0.5 h / 20 °C 4.2: 0.5 h 5.1: caesium carbonate; XPhos; palladium diacetate / 1,4-dioxane; <i>tert</i>-butyl alcohol / 1.5 h / 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3 h / 72 °C 2.1: potassium carbonate / acetone / 4 h / Reflux 3.1: potassium hydroxide / water; methanol / 4 h / 40 °C 4.1: trifluoroacetic anhydride / dichloromethane / 0.5 h / 20 °C 4.2: 0.5 h 5.1: boron tribromide / dichloromethane / -20 °C / Inert atmosphere 6.1: caesium carbonate; XPhos; palladium diacetate / 1,4-dioxane; <i>tert</i>-butyl alcohol / 1.5 h / 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3 h / 72 °C 2.1: potassium carbonate / acetone / 4 h / Reflux 3.1: potassium hydroxide / water; methanol / 4 h / 40 °C 4.1: trifluoroacetic anhydride / dichloromethane / 0.5 h / 20 °C 4.2: 0.5 h 5.1: boron tribromide / dichloromethane / -20 °C / Inert atmosphere 6.1: potassium carbonate / acetone / 6 h / Reflux; Inert atmosphere 7.1: caesium carbonate; XPhos; palladium diacetate / 1,4-dioxane; <i>tert</i>-butyl alcohol / 5 h / 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3 h / 72 °C 2.1: potassium carbonate / acetone / 4 h / Reflux 3.1: potassium hydroxide / water; methanol / 4 h / 40 °C 4.1: trifluoroacetic anhydride / dichloromethane / 0.5 h / 20 °C 4.2: 0.5 h 5.1: boron tribromide / dichloromethane / -20 °C / Inert atmosphere 6.1: potassium carbonate / acetone / 6 h / Reflux; Inert atmosphere 7.1: caesium carbonate; XPhos; palladium diacetate / 1,4-dioxane; <i>tert</i>-butyl alcohol / 6 h / 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3 h / 72 °C 2.1: potassium carbonate / acetone / 4 h / Reflux 3.1: potassium hydroxide / water; methanol / 4 h / 40 °C 4.1: trifluoroacetic anhydride / dichloromethane / 0.5 h / 20 °C 4.2: 0.5 h 5.1: boron tribromide / dichloromethane / -20 °C / Inert atmosphere 6.1: potassium carbonate / acetone / 6 h / Reflux; Inert atmosphere 7.1: caesium carbonate; XPhos; palladium diacetate / 1,4-dioxane; <i>tert</i>-butyl alcohol / 6 h / 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 3 h / 72 °C 2.1: potassium carbonate / acetone / 4 h / Reflux 3.1: potassium hydroxide / water; methanol / 4 h / 40 °C 4.1: trifluoroacetic anhydride / dichloromethane / 0.5 h / 20 °C 4.2: 0.5 h 5.1: boron tribromide / dichloromethane / -20 °C / Inert atmosphere 6.1: potassium carbonate / N,N-dimethyl-formamide / 6 h / Reflux; Inert atmosphere 7.1: caesium carbonate; XPhos; palladium diacetate / 1,4-dioxane; <i>tert</i>-butyl alcohol / 4 h / 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With copper(I) oxide; di-tert-butyl peroxide In <i>tert</i>-butyl alcohol at 120℃; for 24h; Sealed tube; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 2 h / Heating / reflux 2.1: ammonia / methanol / 2 h / 125 °C 3.1: boron tribromide / dichloromethane / 4 h / 20 °C 3.2: pH 6.5 4.1: potassium carbonate; potassium iodide / acetone; toluene / Heating / reflux 5.1: N,N-diethylaniline / 210 °C 6.1: iodine; sodium nitrite / 1-Methylpyrrolidine; water / 3 h / 0 °C 7.1: sodium tetrahydroborate; silica gel / chloroform; isopropyl alcohol / 2 h 8.1: hydrazine / nickel / tetrahydrofuran; ethanol / 4 h 9.1: sodium cyanoborohydride; acetic acid / methanol / 2 h / 20 °C 10.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 2 h / Heating / reflux 2.1: ammonia / methanol / 2 h / 125 °C 3.1: boron tribromide / dichloromethane / 4 h / 20 °C 3.2: pH 6.5 4.1: potassium carbonate; potassium iodide / acetone; toluene / Heating / reflux 5.1: N,N-diethylaniline / 210 °C 6.1: iodine; sodium nitrite / 1-Methylpyrrolidine; water / 3 h / 0 °C 7.1: sodium tetrahydroborate; silica gel / chloroform; isopropyl alcohol / 2 h 8.1: hydrazine / nickel / tetrahydrofuran; ethanol / 4 h 9.1: sodium cyanoborohydride; acetic acid / methanol / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 2 h / Heating / reflux 2.1: ammonia / methanol / 2 h / 125 °C 3.1: boron tribromide / dichloromethane / 4 h / 20 °C 3.2: pH 6.5 4.1: potassium carbonate; potassium iodide / acetone; toluene / Heating / reflux 5.1: N,N-diethylaniline / 210 °C 6.1: iodine; sodium nitrite / 1-Methylpyrrolidine; water / 3 h / 0 °C 7.1: sodium tetrahydroborate; silica gel / chloroform; isopropyl alcohol / 2 h 8.1: hydrazine / nickel / tetrahydrofuran; ethanol / 4 h 9.1: sodium cyanoborohydride; acetic acid / methanol / 1.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 2 h / Heating / reflux 2.1: ammonia / methanol / 2 h / 125 °C 3.1: boron tribromide / dichloromethane / 4 h / 20 °C 3.2: pH 6.5 4.1: potassium carbonate; potassium iodide / acetone; toluene / Heating / reflux 5.1: N,N-diethylaniline / 210 °C 6.1: iodine; sodium nitrite / 1-Methylpyrrolidine; water / 3 h / 0 °C 7.1: sodium tetrahydroborate; silica gel / chloroform; isopropyl alcohol / 2 h 8.1: hydrazine / nickel / tetrahydrofuran; ethanol / 4 h 9.1: sodium cyanoborohydride; acetic acid / methanol / 1.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 2 h / Heating / reflux 2.1: ammonia / methanol / 2 h / 125 °C 3.1: boron tribromide / dichloromethane / 4 h / 20 °C 3.2: pH 6.5 4.1: potassium carbonate; potassium iodide / acetone; toluene / Heating / reflux 5.1: N,N-diethylaniline / 210 °C 6.1: iodine; sodium nitrite / 1-Methylpyrrolidine; water / 3 h / 0 °C 7.1: sodium tetrahydroborate; silica gel / chloroform; isopropyl alcohol / 2 h 8.1: hydrazine / nickel / tetrahydrofuran; ethanol / 4 h 9.1: sodium cyanoborohydride; acetic acid / methanol / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 2 h / Heating / reflux 2.1: ammonia / methanol / 2 h / 125 °C 3.1: boron tribromide / dichloromethane / 4 h / 20 °C 3.2: pH 6.5 4.1: potassium carbonate; potassium iodide / acetone; toluene / Heating / reflux 5.1: N,N-diethylaniline / 210 °C 6.1: iodine; sodium nitrite / 1-Methylpyrrolidine; water / 3 h / 0 °C 7.1: sodium tetrahydroborate; silica gel / chloroform; isopropyl alcohol / 2 h 8.1: hydrazine / nickel / tetrahydrofuran; ethanol / 4 h 9.1: sodium cyanoborohydride; acetic acid / methanol / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 2 h / Heating / reflux 2.1: ammonia / methanol / 2 h / 125 °C 3.1: boron tribromide / dichloromethane / 4 h / 20 °C 3.2: pH 6.5 4.1: potassium carbonate; potassium iodide / acetone; toluene / Heating / reflux 5.1: N,N-diethylaniline / 210 °C 6.1: iodine; sodium nitrite / 1-Methylpyrrolidine; water / 3 h / 0 °C 7.1: sodium tetrahydroborate; silica gel / chloroform; isopropyl alcohol / 2 h 8.1: hydrazine / nickel / tetrahydrofuran; ethanol / 4 h 9.1: sodium cyanoborohydride; acetic acid / methanol / 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 2 h / Heating / reflux 2.1: ammonia / methanol / 2 h / 125 °C 3.1: boron tribromide / dichloromethane / 4 h / 20 °C 3.2: pH 6.5 4.1: potassium carbonate; potassium iodide / acetone; toluene / Heating / reflux 5.1: N,N-diethylaniline / 210 °C 6.1: iodine; sodium nitrite / 1-Methylpyrrolidine; water / 3 h / 0 °C 7.1: sodium tetrahydroborate; silica gel / chloroform; isopropyl alcohol / 2 h 8.1: hydrazine / nickel / tetrahydrofuran; ethanol / 4 h 9.1: sodium cyanoborohydride; acetic acid / methanol / 0.67 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 2 h / Heating / reflux 2.1: ammonia / methanol / 2 h / 125 °C 3.1: boron tribromide / dichloromethane / 4 h / 20 °C 3.2: pH 6.5 4.1: potassium carbonate; potassium iodide / acetone; toluene / Heating / reflux 5.1: N,N-diethylaniline / 210 °C 6.1: iodine; sodium nitrite / 1-Methylpyrrolidine; water / 3 h / 0 °C 7.1: sodium tetrahydroborate; silica gel / chloroform; isopropyl alcohol / 2 h 8.1: hydrazine / nickel / tetrahydrofuran; ethanol / 4 h 9.1: sodium cyanoborohydride; acetic acid / methanol / 2 h / 20 °C 10.1: sodium cyanoborohydride; acetic acid / methanol / 4 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 11 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 2 h / Heating / reflux 2.1: ammonia / methanol / 2 h / 125 °C 3.1: boron tribromide / dichloromethane / 4 h / 20 °C 3.2: pH 6.5 4.1: potassium carbonate; potassium iodide / acetone; toluene / Heating / reflux 5.1: N,N-diethylaniline / 210 °C 6.1: iodine; sodium nitrite / 1-Methylpyrrolidine; water / 3 h / 0 °C 7.1: sodium tetrahydroborate; silica gel / chloroform; isopropyl alcohol / 2 h 8.1: hydrazine / nickel / tetrahydrofuran; ethanol / 4 h 9.1: sodium cyanoborohydride; acetic acid / methanol / 2 h / 20 °C 10.1: sodium cyanoborohydride; acetic acid / methanol / 4 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 11 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 2 h / Heating / reflux 2.1: ammonia / methanol / 2 h / 125 °C 3.1: boron tribromide / dichloromethane / 4 h / 20 °C 3.2: pH 6.5 4.1: potassium carbonate; potassium iodide / acetone; toluene / Heating / reflux 5.1: N,N-diethylaniline / 210 °C 6.1: iodine; sodium nitrite / 1-Methylpyrrolidine; water / 3 h / 0 °C 7.1: sodium tetrahydroborate; silica gel / chloroform; isopropyl alcohol / 2 h 8.1: hydrazine / nickel / tetrahydrofuran; ethanol / 4 h 9.1: sodium cyanoborohydride; acetic acid / methanol / 2 h / 20 °C 10.1: sodium cyanoborohydride; acetic acid / methanol / 4 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 2 h / Heating / reflux 2.1: ammonia / methanol / 2 h / 125 °C 3.1: boron tribromide / dichloromethane / 4 h / 20 °C 3.2: pH 6.5 4.1: potassium carbonate; potassium iodide / acetone; toluene / Heating / reflux 5.1: N,N-diethylaniline / 210 °C 6.1: iodine; sodium nitrite / 1-Methylpyrrolidine; water / 3 h / 0 °C 7.1: sodium tetrahydroborate; silica gel / chloroform; isopropyl alcohol / 2 h 8.1: hydrazine / nickel / tetrahydrofuran; ethanol / 4 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With chloro(2-dicyclohexylphosphino-2’,6’-diisopropoxy-1,1’-biphenyl)[2-(2’-amino-1,1’-biphenyl)]palladium(ll); caesium carbonate In toluene at 115℃; for 16h; Inert atmosphere; | 1 Step 1 - Methyl 5-methoxy-2-methyl-benzoate A mixture of methyl 2-bromo-5-methoxy-benzoate (5.00 g, 20.4 mmol, CAS 35450-36-3), methylboronic acid (24.4 g, 408 mmol, CAS 13061-96-6), [2-(2- aminophenyl)phenyl]-chloro-palladium;dicyclohexyl-[2-(2,6- diisopropoxyphenyl)phenyl]phosphane (1.58 g, 2.04 mmol) and Cs2CO3 (19.9 g, 61.2 mmol) in toluene (100 mL) was stirred at 115 °C for 16 hours. On completion, after cooled to 25 °C, the mixture was diluted with water (100 mL), and extracted with EA (3 X 50 mL). The combined organic layer was washed with brine (30 mL), dried over Na2SO4, filtered and concentrated in vacuo to give a residue. The residue was purified by column chromatography on silica gel (PE: EA = 100:1 - 50:1) to give the title compound (3.50 g, 95% yield) as light yellow oil.1H NMR (400 MHz, CDCl3) d 7.45 (d, J = 2.8 Hz, 1H), 7.15 (d, J = 8.4 Hz, 1H), 6.97 (dd, J = 2.8, 8.4 Hz, 1H), 3.90 (s, 3H), 3.83 (s, 3H), 2.53 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate In acetone at 20℃; for 1h; |
Tags: 73502-03-1 synthesis path| 73502-03-1 SDS| 73502-03-1 COA| 73502-03-1 purity| 73502-03-1 application| 73502-03-1 NMR| 73502-03-1 COA| 73502-03-1 structure
[ 35598-05-1 ]
Methyl 4-methoxy-2-methylbenzoate
Similarity: 1.00
[ 108298-35-7 ]
Dimethyl 5-methoxy-3-methylphthalate
Similarity: 1.00
[ 37934-88-6 ]
Methyl 4-methoxy-2,6-dimethylbenzoate
Similarity: 1.00
[ 35598-05-1 ]
Methyl 4-methoxy-2-methylbenzoate
Similarity: 1.00
[ 108298-35-7 ]
Dimethyl 5-methoxy-3-methylphthalate
Similarity: 1.00
[ 37934-88-6 ]
Methyl 4-methoxy-2,6-dimethylbenzoate
Similarity: 1.00
[ 35598-05-1 ]
Methyl 4-methoxy-2-methylbenzoate
Similarity: 1.00
[ 108298-35-7 ]
Dimethyl 5-methoxy-3-methylphthalate
Similarity: 1.00
[ 37934-88-6 ]
Methyl 4-methoxy-2,6-dimethylbenzoate
Similarity: 1.00
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