Alternatived Products of [ 18643-84-0 ] Product Details of [ 18643-84-0 ]
| CAS No. : | 18643-84-0 | MDL No. : | MFCD00060639 |
| Formula : |
C10H9ClO4 | Boiling Point : | - |
| Linear Structure Formula : | - | InChI Key : | - |
| M.W : |
228.63
| Pubchem ID : | - |
| Synonyms : | |
Application In Synthesis of [ 18643-84-0 ]
* 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.
- Downstream synthetic route of [ 18643-84-0 ]
- 1
[ 7697-25-8 ]
[ 18643-84-0 ]
- 2
- [ 18643-84-0 ]
[ 431888-57-2 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|
| 62% | With boron tribromide; In dichloromethane; at -5 - 20℃; for 18.5h; | A solution of dimethyl 2-chloroterephthalate (2.5 g, 1 1 mmol) in DCM (20 mL) was cooled to -5C and treated with BBr3 (1 M in DCM) (1 1 mL, 1 1 mmol) dropwise over 30 min. The mixture was then warmed to RT and stirred for 18 h. The mixture was poured into ice, warmed to RT and the pH was adjusted to 8 by the addition of solid NaHC03. The aq. solution was washed with EtOAc (50 mL), acidified by the addition of 1 M HCI and extracted with EtOAc (160 mL). The organic solution was washed with brine (80 mL), dried over MgS04, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (120 g, 0-10% [MeOH 5% AcOH] in DCM) to afford the title compound (2) (1.5 g, 62%) as white solid: m/z 215 [M+H]+ (ES+), 213 [M-H]- (ES-); NMR (400 MHz, DMSO-de) delta: 13.79 (1 H, br. s), 8.00 - 7.95 (2H, m), 7.90 - 7.88 (1 H, m), 3.89 (3H, s) |
| With boron tribromide; In dichloromethane; at 0 - 20℃; | 20 g of dimethyl 2-chloroterephthalate was cooled to 0C in DCM and 87 mL of a IM in DCM solution Of BBr3 was added dropwise over several hours. The reaction mixture was subsequently warmed to room temperature and stirred until complete. Following basic workup, 2-chloro-4-(methoxycarbonyl)benzoic acid was purified by ISCO Combi-Flash. |
| With boron tribromide; In dichloromethane; at 0 - 20℃; | 67 mL of 2-chloro-1,4-dimethylbenzene and 356 g of Potassium Permanganate were refluxed in 1.5 L of H2O for several hours and monitored for disappearance of starting material by TLC. The Potassium Permanganate was filtered and the reaction mixture was acidified and filtered to yield 2-chloroterephthalic acid. 46.8 g of 2-chloroterephthalic acid was treated with a saturated HCl gas solution in MeOH overnight at room temperature. The reaction mixture was concentrated, subjected to basic workup and dried to yield the dimethyl 2-chloroterephthalate. 20 g of dimethyl 2-chloroterephthalate was cooled to 0 C. in DCM and 87 mL of a 1 M in DCM solution of BBr3 was added dropwise over several hours. The reaction mixture was subsequently warmed to room temperature and stirred until complete. Following basic workup, 2-chloro-4-(methoxycarbonyl)benzoic acid was purified by ISCO Combi-Flash. 959 mg of 2-chloro-4-(methoxycarbonyl)benzoic acid was coupled to 750 mg of 4-chloro-3-(pyridin-2-yl)aniline via procedure G. 1 g of methyl 3-chloro-4-(4-chloro-3-(pyridin-2-yl)phenylcarbamoyl)benzoate was hydrolyzed via Procedure M to give 3-chloro-4-(4-chloro-3-(pyridin-2-yl)phenylcarbamoyl)benzoic acid. 50 mg of 3-chloro-4-(4-chloro-3-(pyridin-2-yl)phenylcarbamoyl)benzoic acid was coupled to tert-butylamine via Procedure G. The product was purified on reverse phase HPLC to yield N4-tert-butyl-2-chloro-N1-(4-chloro-3-(pyridin-2-yl)phenyl)terephthalamide. MS (Q1) 443.2 (M)+. |
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