Structure of 220141-23-1
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CAS No. : | 220141-23-1 |
Formula : | C9H6F4O2 |
M.W : | 222.14 |
SMILES Code : | COC(=O)C1=C(C=C(F)C=C1)C(F)(F)F |
MDL No. : | MFCD06203708 |
InChI Key : | BNUYNCHJMOWGOH-UHFFFAOYSA-N |
Pubchem ID : | 15541084 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 |
* 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 |
---|---|---|
18.0 g (65.9%) | In N-methyl-acetamide; methanol; | Step A. 4-Fluoro-2-trifluoromethylbenzoic acid methyl ester A suspension of <strong>[141179-72-8]4-fluoro-2-trifluoromethylbenzoic acid</strong> (25.6 g, 123.0 mmol) in dichoromethane (250 mL) containing a few drops of dimethylformamide was treated dropwise under nitrogen with oxalyl chloride (11.3 mL, 129.5 mmol). After the gas evolution subsided, the reaction mixture was refluxed for an additional 15 minutes. The mixture was cooled and methanol (50 mL) was added. After stirring for 2 hrs, the reaction was concentrated, and the residue was partitioned between dichloromethane and water. The organic phase was washed with saturated aqueous sodium bicarbonate, dried over sodium sulfate, and evaporated t o dryness to give 18.0 g (65.9%) of the title compound as a golden oil. NMR (DMSO-d6, 400 MHz): delta 3.85 (s, 3H), 7.67 (m, 1H), 7.80 (m, 1H), 7.95 (m, 1H)MS (EI, m/z): 222 [M]+ |
In N-methyl-acetamide; methanol; dichloromethane; | Step A. 4-Fluoro-2-trifluoromethylbenzoic acid methyl ester A suspension of <strong>[141179-72-8]4-fluoro-2-trifluoromethylbenzoic acid</strong> (25.6 g, 123.0 mmol) in dichloromethane (250 mL) containing a few drops of dimethylformamide was treated dropwise under nitrogen with oxalyl chloride (11.3 mL, 129.5 mmol). After the gas evolution subsided, the reaction mixture was refluxed for an additional 15 minutes. The mixture was cooled and methanol (50 mL) was added. After stirring for 2 hrs, the reaction was concentrated, and the residue was partitioned between dichloromethane and water. The organic phase was washed with saturated aqueous sodium bicarbonate, dried over sodium sulfate, and evaporated to dryness to give 18.0 g of the title compound as a golden oil. NMR (DMSO-d6, 400 MHz): delta 3.85 (s, 3H), 7.67 (m, 1H), 7.80 (m, 1H), 7.95 (m, 1H) MS (EI, m/z): 222 [M]+ | |
18.0 g (65.9%) | In N-methyl-acetamide; methanol; dichloromethane; | Step A. 4-Fluoro-2-trifluoromethylbenzoic acid methyl ester A suspension of <strong>[141179-72-8]4-fluoro-2-trifluoromethylbenzoic acid</strong> (25.6 g, 123.0 mmol) in dichloromethane (250 mL) containing a few drops of dimethylformamide was treated dropwise under nitrogen with oxalyl chloride (11.3 mL, 129.5 mmol). After the gas evolution subsided, the reaction mixture was refluxed for an additional 15 minutes. The mixture was cooled and methanol (50 mL) was added. After stirring for 2 hrs, the reaction was concentrated, and the residue was partitioned between dichloromethane and water. The organic phase was washed with saturated aqueous sodium bicarbonate, dried over sodium sulfate, and evaporated to dryness to give 18.0 g (65.9%) of the title compound as a golden oil. NMR (DMSO-d6, 400 MHz): delta 3.85 (s, 3H), 7.67 (m, 1H), 7.80 (m, 1H), 7.95 (m, 1H)MS (EI, m/z): 222 [M]+. |
In N-methyl-acetamide; methanol; dichloromethane; | Step A. 4-Fluoro-2-trifluoromethylbenzoic acid methyl ester A suspension of <strong>[141179-72-8]4-fluoro-2-trifluoromethylbenzoic acid</strong> (25.6 g, 123.0 mmol) in dichloromethane (250 mL) containing a few drops of dimethylformamide was treated dropwise under nitrogen with oxalyl chloride (11.3 mL, 129.5 mmol). After the gas evolution subsided, the reaction mixture was refluxed for an additional 15 minutes. The mixture was cooled and methanol (50 mL) was added. After stirring for 2 hrs, the reaction was concentrated, and the residue was partitioned between dichloromethane and water. The organic phase was washed with saturated aqueous sodium bicarbonate, dried over sodium sulfate, and evaporated to dryness to give 18.0 g of the title compound as a golden oil. NMR (DMSO-d6, 400 MHz): delta3.85 (s, 3H), 7.67 (m, 1H), 7.80 (m, 1H), 7.95 (m, 1H) MS (EI, m/z): 222 [M]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65.9% | A suspension of <strong>[141179-72-8]4-fluoro-2-trifluoromethylbenzoic acid</strong> (25.6 g, 123.0 mmol) in dichloromethane (250 mL) containing a few drops of dimethylformamide was treated dropwise under nitrogen with oxalyl chloride (11.3 mL, 129.5 mmol). After the gas evolution subsided, the reaction mixture was refluxed for an additional 15 minutes. The mixture was cooled and methanol (50 mL) was added. After stirring for 2 hrs, the reaction was concentrated, and the residue was partitioned between dichloromethane and water. The organic phase was washed with saturated aqueous sodium bicarbonate, dried over sodium sulfate, and evaporated to dryness to give 18.0 g (65.9%) of the title compound as a golden oil. NMR (DMSO-d6, 400 MHz): delta 3.85 (s, 3H), 7.67 (m, 1H), 7.80 (m, 1H), 7.95 (m, 1H)MS (EI, m/z): 222 [M]+ The aqueous layer was acidified with 2 N hydrochloric acid and the white solid was collected by filtration to give 7.5 g (29.3%) of the starting <strong>[141179-72-8]4-fluoro-2-trifluoromethylbenzoic acid</strong> | |
REFERENCE EXAMPLE 93; Methyl 4-(3-methyl-pyrazol-1-yl)-2-trifluoromethyl-benzoate; Step a) methyl 4-fluoro-2-trifluoromethylbenzoate: A suspension of <strong>[141179-72-8]4-fluoro-2-trifluoromethylbenzoic acid</strong> (25.6 g) and a few drops of dimethylformamide in dichloromethane (250 ml) was treated dropwise under nitrogen with oxalyl chloride (11.3 ml).. After gas evolution subsided, the reaction mixture was refluxed for an additional 15 minutes.. The reaction was cooled and methanol (50 ml) was added.. After stirring for 2 hours, the reaction was concentrated in vacuo, and the residue was partitioned between dichloromethane and water.. The organic phase was washed with saturated sodium bicarbonate, dried over anhydrous sodium sulfate, and evaporated to dryness to give 18.0 g of the title compound as a golden oil. MS, (EI) m/z: 222 (M)+. The aqueous layer was acidified with 2 N hydrochloric acid to give a colorless solid which was collected by filtration to give 7.5 g of the starting benzoic acid. | ||
Step a) Methyl 4-fluoro-2-trifluoromethylbenzoate: A suspension of <strong>[141179-72-8]4-fluoro-2-trifluoromethylbenzoic acid</strong> (25.6 g) and a few drops of dimethylformamide in dichloromethane (250 ml) was treated dropwise under nitrogen with oxalyl chloride (11.3 ml). After gas evolution subsided, the reaction mixture was refluxed for an additional 15 minutes. The reaction was cooled and methanol (50 ml) was added. After stirring for 2 hours, the reaction was concentrated in vacuo, and the residue was partitioned between dichloromethane and water. The organic phase was washed with saturated sodium bicarbonate, dried over anhydrous sodium sulfate, and evaporated to dryness to give 18.0 g of the title compound as a golden oil. MS, (EI) m/z: 222 (M)+. The aqueous layer was acidified with 2 N hydrochloric acid to give a colorless solid which was collected by filtration to give 7.5 g of the starting benzoic acid. |
With sulfuric acid; at 0℃; for 48h;Reflux; | Preparation Example 17 To a solution of <strong>[141179-72-8]4-fluoro-2-(trifluoromethyl)benzoic acid</strong> in MeOH were added concentrated sulfuric acid at 0C. The reaction mixture was heated and refluxed for 2 days. The reaction mixture was concentrated under reduced pressure and the residue was diluted with EtOAc. The organic layer was washed with a saturated aqueous NaHCO3 solution, dried over MgSO4, and then concentrated under reduced pressure to obtain methyl 4-fluoro-2-(trifluoromethyl)benzoate as a colorless oily substance. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; diethyl ether; chloroform; for 2h; | To a solution of <strong>[141179-72-8]4-fluoro-2-(trifluoromethyl)benzoic acid</strong> (2.02 g, 9.71 mmol, Aldrich) in methanol and chloroform (1 :1 , 32 ml) was added a 2 M TMS-diazomethane in ether (~ 7ml) in portions, over about 2 h, allowing the solution to cool down between additions. The solution was evaporated in vacuo and the residue dissolved in chloroform (-20 ml). The solution was evaporated in vacuo to give methyl 4-fluoro-2- (trifluoromethyl)benzoate as a slightly yellow-brown liquid (2.07 g). |
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