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CAS No. : | 31719-77-4 | MDL No. : | MFCD00191922 |
Formula : | C8H7ClO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PBSUMBYSVFTMNG-UHFFFAOYSA-N |
M.W : | 170.59 | Pubchem ID : | 241752 |
Synonyms : |
|
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | 3261 |
Hazard Statements: | H302+H312+H332-H314 | Packing Group: | Ⅱ |
GHS Pictogram: |
* 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 |
---|---|---|
90% | With sulfuric acid; for 12h;Heating / reflux; | Example 17 Ethyl 3-(chloromethyl)benzoate 13a (Scheme 7) To a stirred solution of 3-(chloromethyl)benzoic acid 23 (0.01 mol, 1.70 g) in anhydrous ethanol (20 ml) was added few drops (approximately 0.2 ml) concentrated sulfuric acid was added and the resulting mixture was refluxed for 12 hours. The reaction mixture was concentrated on rotavapor and the residue was diluted with ethyl acetate (50 ml). The ethyl acetate solution was washed successively with water, saturated sodium bicarbonate (NaHCO3), water, and dried over anhydrous magnesium sulfate (MgSO4). Evaporation of the solvent gave the target ester 13a as colorless oil in 90% yield (1.78 g). The ester 13a was taken to next step without any further purification. 1H NMR (400 MHz, CDCl3): delta 1.30 (3H, t, J=7.2 Hz); 4.29 (2H, t, J=7.2 Hz); 4.83 (2H, s); 7.53 (1H, m); 7.69 (1H, broad d); 7.90 (1H, broad d); 8.01 (1H, s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step 1 3-chloromethylbenzoic acid (5. 9mmol) was dissolved in DMF and [CARBONYLDIIMIDAZOLE] (6. 2mmol) added. After 5 minutes the amine (5. 8mmol) was added and the reaction stirred at room temperature for 4h. The reaction mixture was diluted with water and extracted with [DICHLOROMETHANE.] The combined organics were dried over [MGS04,] filtered, and the solvent removed. The crude residue was purified by flash chromatography. Step 2 The product from step 1 (1. [6MMOL)] was dissolved in DMF along with the nitrothiopyridine (1. [6MMOL).] To this solution was added Hunig's base (3. 1 mmol) and the reaction stirred at room temperature overnight. The reaction mixture was treated with acetic acid solution and the product extracted with [DICHLOROMETHANE.] The combined organics were dried [OVER MGS04, FILTERED,] and the solvent removed. The crude residue was purified by flash chromatography. Step 3 The product from step 2 (0. [36MMOL)] was dissolved in ethanol and tin chloride dihydrate added. The reaction mixture was heated at [70C] for 2h. The residue was diluted with water and the product extracted with DCM. The combined organics were dried over MgS04, filtered, and the solvent removed. The crude product was used in the next reaction. Step 4 The product from step 3 (0. [07MMOL)] was dissolved in DCM and the acid chloride [(0.] [08MMOL)] added. To this was added [PS-DIEA] and PS-DMAP and the reaction stirred at RT overnight. The crude product was filtered and the solvent removed. The product was purified by flash chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | With potassium carbonate; In acetonitrile; | To a stirred suspension of intermediate 12.2 (100 mg, 0.43 mmol) and K2C03 (178 mg, 1.29 mmol) in CH3CN (15 mL) was added 3-(chloromethyl)benzoic acid (74 mg, 0.43 mmol). Stirring was continued overnight at reflux. The volatiles were removed under vacuo. The crude was taken up with water, washed with EtOAc, acidified to pH 3 and extracted with EtOAc (3 x 50 mL). Titration with a mixture of Et20/Acetone afforded compound 14 (30 mg, 0.088 mmol) as white solid. Yield 21%. 1HNMR(400 MHz, DMSO) delta 4.59 (s, 2H), 6.69 (s, 1H), 7.41 (m, 1H), 7.46 (m, 3H), 7.71 (d, J= 7.5 Hz, 1H), 7.81 (d, J= 7.74 Hz, 1H),8.06 (m, 3H), 12.85 (s, 2H). 13C NMR (100 MHz, DMSO) delta 33.8, 127.3, 127.3, 128.5, 129.1,129.2, 130.1, 131.0, 131.3, 131.5, 133.6, 136.3, 138.8, 167.5. |
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