| 90% |
With tris-(dibenzylideneacetone)dipalladium(0); potassium hydroxide; tert-butyl XPhos; In 1,4-dioxane; water; at 100℃;Inert atmosphere; |
A 1L three-necked round-bottomed flask equipped with a magnetic stir bar was charged with di-tert-butyl (2', 4', 6'-triisopropyl- [1, 1'-biphenyl] -2-yl) phosphine (8.37 g, 19.70 mmol) , tris (dibenzylideneacetone) dipalladium (4.51 g, 4.92 mmol) and potassium hydroxide (41.4 g, 739 mmol) . The flask was evacuated and backfilled with nitrogen. Separately, dioxane (150 mL) , 2-bromo-5-fluoro-1, 3-dimethylbenzene (50 g, 246 mmol) and water (150 mL) were flow purged with nitrogen for about 30 minutes and were transferred to the reaction flask via a cannula. The reaction vessel was heated to about 100 C and stirred overnight. The reaction mixture was cooled to ambient temperature. The reaction mixture was acidified to pH 2 by adding 6N HCl and the product was extracted with dichloromethane (3 x 250 mL) . The combined organic layers were stirred with mercaptopropyl silica gel for about 30 minutes, dried over anhydrous magnesium sulfate, filtered, and concentrated to afford the title compound as a white solid. (31.2 g, 223 mmol, 90% yield) |
| 90% |
With tris-(dibenzylideneacetone)dipalladium(0); water; potassium hydroxide; tert-butyl XPhos; In 1,4-dioxane;Inert atmosphere; |
A 1L three-necked round-bottomed flask equipped with a magnetic stir bar was charged with di-tert-butyl(2?,4?,6?-triisopropyl-[ 1,1 ?-biphenyll -2-yl)phosphine (8.37 g, 19.70mmol), tris(dibenzylideneacetone)dipalladium (4.51 g, 4.92 mmol) and potassium hydroxide (41.4 g, 739 mmol). The flask was evacuated and backfilled with nitrogen. Separately, dioxane (150 mL), <strong>[14659-58-6]2-bromo-5-fluoro-1,3-dimethylbenzene</strong> (50 g, 246 mmol) and water (150 mL) were flow purged with nitrogen for about 30 minutes and were transferred to the reaction flask via a cannula. The reaction vessel was heated to about 100 C and stirredovernight. The reaction mixture was cooled to ambient temperature, acidified to pH 2 by adding 6N HC1, and extracted with dichloromethane (3 x 250 mL). The combined organic layers were stirred with mercaptopropyl silica gel for about 30 minutes, dried over anhydrous magnesium sulfate, filtered, and concentrated to provide the title compound as a white solid. (31.2 g, 223 mmol, 90% yield) |
| 86% |
|
n-Butyllithium (11 mL, 17.7 mmol, 1.6 M) was added dropwise to <strong>[14659-58-6]2-bromo-5-fluoro-1,3-dimethylbenzene</strong> (3 g, 14.8 mmol) in tetrahydrofuran (30 mL). ) in solution.The reaction solution was stirred at -78 C for 30 minutes under nitrogen atmosphere.Then trimethyl borate (1.84 g, 17.7 mmol). After the completion of the dropwise addition, the reaction solution was slowly warmed to room temperature and stirred for 12 hours. A solution of sodium hydroxide (0.88 g, 22 mmol) in hydrogen peroxide (24 mL, 30% w/w) was added dropwise to the reaction mixture at -15 C. After completion of the dropwise addition, the reaction mixture was stirred at room temperature for 3 hr. Ethyl acetate (75 mL * 2) was extracted, washed with saturated brine (100 mL*3), and evaporated After column separation (petroleum ether: ethyl acetate = 5:1), 4-fluoro-2,6-dimethylphenol (1.8 g, 12.73 mmol, yield: 86%) was obtained. |
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