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With potassium fluoride;palladium diacetate; In tetrahydrofuran;
EXAMPLE 34 Synthesis of 4-hydroxybiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.02 mmol, 2.0 mol percent), phenylboronic acid (183 mg, 1.5 mmol), potassium fluoride (174 mg, 3.0 mmol), and 4-bromophenol (173 mg, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) was added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl bromide had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL), filtered through celite, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 154 mg (91percent) of the title compound.
154 mg (91%)
With potassium fluoride;palladium diacetate; In tetrahydrofuran;
Example 34 Synthesis of 4-hydroxybiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.02 mmol, 2.0 mol percent), phenylboronic acid (183 mg, 1.5 mmol), potassium fluoride (174 mg, 3.0 mmol), and 4-bromophenol (173 mg, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) was added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl bromide had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL), filtered through celite, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 154 mg (91percent) of the title compound.
With dmap; 2,6-di-tert-butyl-4-methyl-phenol; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃;
The 4 - (6-acryloxy-1-hexyloxy) benzoic acid (corporate SYNTHONChemicals) 29.2g (100mmol), 4-hydroxy-biphenyl 17.0g (100mmol), DMAP0.6g and a small amount of BHT to the mixed suspension under stirring at room temperature in dichloromethane 200 ml in, adding by DCC24.0g (116mmol) dissolved in the dichloromethane 100 ml solution in which a, stirring overnight. Filtering precipitation of urea of DCC, the filtrate for the sequentially 0.5mol/L hydrochloric acid 150 ml, saturated aqueous solution of sodium bicarbonate 150 ml, saturated salt water 150 ml various washing 2 times, after drying with magnesium sulfate, solvent is removed by distillation, recrystallization with ethanol refined, polymerizable compound to obtain a target of (M2) 39.6g (yield 89percent).
1,1-dimethylethyl (S)-4-[[(3-biphenyloxy)]methyl]-2,2-dimethyl-3-oxazolidinecarboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
51%
With di-isopropyl azodicarboxylate; triphenylphosphine; In toluene; at 80℃; for 3h;
General procedure: To a stirred solution of 39 (0.100g, 0.433mmol), appropriate substituted phenol (0.649mmol) and PPh3 (0.182g, 0.693mmol) in anhydrous toluene (5mL) was added DIAD (0.14mL, 0.693mmol) at 80C. After 3h, EtOAc (40mL) was added to the resulting solution. The organic layer was washed with 0.5M aqueous NaOH (40mL) and water (2×40mL), dried over Na2SO4, filtered and concentrated. The residue was purified by flash silica gel column chromatography eluting with Hexanes/EtOAc (9:1) or (95:5).
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