Alternatived Products of [ 136897-64-8 ]
Product Details of [ 136897-64-8 ]
CAS No. : | 136897-64-8 |
MDL No. : | MFCD06658272 |
Formula : |
C9H7F3O3
|
Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | WRNVSUJHRFXTKQ-UHFFFAOYSA-N |
M.W : |
220.15
|
Pubchem ID : | 10656519 |
Synonyms : |
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Safety of [ 136897-64-8 ]
Application In Synthesis of [ 136897-64-8 ]
* 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.
- Upstream synthesis route of [ 136897-64-8 ]
- Downstream synthetic route of [ 136897-64-8 ]
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[ 136897-64-8 ]
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[ 112811-65-1 ]
- 2
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[ 116751-24-7 ]
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[ 74-88-4 ]
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[ 136897-64-8 ]
Yield | Reaction Conditions | Operation in experiment |
91% |
With sodium hydride In N,N-dimethyl-formamide for 18h; |
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With sodium hydride In N,N-dimethyl-formamide |
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Reference:
[1]Sanchez, Joseph P.; Gogliotti, Rocco D.; Domagala, John M.; Gracheck, Stephen J.; Huband, Michael D.; et al.
[Journal of Medicinal Chemistry, 1995, vol. 38, # 22, p. 4478 - 4487]
[2]Baker, William R.; Cai, Shaopei; Dimitroff, Martin; Fang, Liming; Huh, Kay K.; Ryckman, David R.; Shang, Xiao; Shawar, Ribhi M.; Therrien, Joseph H.
[Journal of Medicinal Chemistry, 2004, vol. 47, # 19, p. 4693 - 4709]
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[ 136897-64-8 ]
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[ 112811-66-2 ]
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps
1: aq. NaOH / methanol
2: (COCl)2; DMF / CH2Cl2 |
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Multi-step reaction with 2 steps
1: 61 percent / 1.0 N aq. NaOH / methanol / 3 h / Ambient temperature
2: oxalyl chloride, DMF / CH2Cl2 / 18 h / Ambient temperature |
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Reference:
[1]Baker, William R.; Cai, Shaopei; Dimitroff, Martin; Fang, Liming; Huh, Kay K.; Ryckman, David R.; Shang, Xiao; Shawar, Ribhi M.; Therrien, Joseph H.
[Journal of Medicinal Chemistry, 2004, vol. 47, # 19, p. 4693 - 4709]
[2]Sanchez, Joseph P.; Gogliotti, Rocco D.; Domagala, John M.; Gracheck, Stephen J.; Huband, Michael D.; et al.
[Journal of Medicinal Chemistry, 1995, vol. 38, # 22, p. 4478 - 4487]
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[ 136897-64-8 ]
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[ 112811-71-9 ]
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[ 116751-24-7 ]
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[ 616-38-6 ]
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[ 136897-64-8 ]
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[ 137234-92-5 ]
Yield | Reaction Conditions | Operation in experiment |
91% |
With potassium iodide In N,N-dimethyl acetamide; water |
3 Example 3
Example 3 38.4 g (0.2 mol) of 3-hydroxy-2,4,5-trifluorobenzoic acid, 1.2 g of potassium iodide and 2 g of dibenzo-18-crown-6 and 20 g (0.22 mol) of dimethyl carbonate are dissolved in 250 g of N,N-dimethylacetamide with stirring, the mixture is transferred to an autoclave lined with PTFE, heated to 110° C. with stirring and allowed to react for 18 hours. According to GC, the reaction product does not contain any starting material and only <1% of methyl 3-methoxy-2,4,5-trifluorobenzoate. Excess solvent is distilled off through a short Vigreux column, the remaining oily residue is subjected to fractional distillation, and the substance obtained is stirred with 300 g of hot water. This gives 37.6 g (0.183 mol) of methyl 3-hydroxy-2,4,5-trifluorobenzoate. (91% yield; purity by GC >99%). |
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[ 116751-24-7 ]
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[ 136897-64-8 ]
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[ 137234-92-5 ]
Yield | Reaction Conditions | Operation in experiment |
78% |
With dmap; potassium iodide In water; carbonic acid dimethyl ester |
2 Example 2
Example 2 0.25 g of potassium iodide, 0.5 g of 4-dimethylaminopyridine and 51 g of crude 3-hydroxy-2,4,5-trifluorobenzoic acid (3-hydroxy-2,4,5-trifluorobenzoic acid content 40.3 g, determined by HPLC and corrected for the response factors) are dissolved in 250 g of dimethyl carbonate with stirring, the mixture is transferred to an autoclave lined with PTFE, heated to 145° C. with stirring and allowed to react for 16 hours. It is then cooled and let down. The solution removed from the autoclave is freed from insoluble residue by filtration, and the dimethyl carbonate is distilled off. The resulting mixture contains <1% of methyl 3-methoxy-2,4,5-trifluorobenzoate. Distillation (1 mbar=0.1 kPa) via a splash guard gives 36 g of a pale yellow oil (temperature at the top 107° to 115° C.). This product is stirred with 200 g of hot water. Cooling and separation gives 33.6 g (0.163 mol) of methyl 3-hydroxy-2,4,5-trifluorobenzoate (78% yield; purity by GC/HPLC >99%). |