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With potassium carbonate;palladium on carbon; In ethanol; water; toluene; for 2h;Reflux; Inert atmosphere;
Ethyl 4-iodoethylbenzoate (1) (25.0 g), <strong>[212386-71-5]4-ethoxy-2,3-difluorophenylboronic acid</strong> (2) (20.1 g), potassium carbonate (25.0 g), Pd/C (0.25 g), toluene (100 ml), ethanol (100 ml) and water (100 ml) were put in a reaction vessel under a nitrogen atmosphere, and heated under reflux for 2 hours. The reaction mixture was cooled to 25 C, and then poured into water (500 ml) and toluene (500 ml), and mixed. The mixture was then allowed to stand until it had separated into two phases of organic and aqueous phases. The extraction to an organic phase was carried out. The organic phase obtained was washed with water, and then dried over anhydrous magnesium sulfate. The solution obtained was concentrated under reduced pressure, and the residue obtained was purified by means of column chromatography (silica gel; toluene). The product was further purified by means of recrystallization from ethanol and dried, giving 18.8 g of ethyl 4-ethoxy-2,3-difluoro-4'-biphenylcarboxylate (3). The yield based on the compound (1) was 67.9%.
67.9%
With potassium carbonate;5% Pd(II)/C(eggshell); In ethanol; water; toluene; for 2h;Inert atmosphere; Reflux;
Example 1; Synthesis of 4-ethoxy-2,3-difluoro-4'-[2,3-difluoro-4-(4-pentylcyclohexyl)phenoxymethyl]-1,1'-biphenyl (No. 1123) [Show Image] First Step: 4-Iodoethyl benzoate (1) (25.0 g), <strong>[212386-71-5]4-ethoxy-2,3-difluorophenylboronic acid</strong> (2) (20.1 g), potassium carbonate (25.0 g), palladium on carbon (NX type of 5%Pd/C; 50% wet; made by N. E. Chemcat; hereinafter referred to as Pd/C) (0.25 g), toluene (100 ml), ethanol (100 ml) and water (100 ml) were put in a reaction vessel under a nitrogen atmosphere, and heated under reflux for 2 hours. The reaction mixture was cooled to 25 C, and then poured into water (500 ml) and toluene (500 ml), and mixed. The mixture was then allowed to stand until it had separated into two phases of organic and aqueous phases, and extraction into an organic phase was carried out. The organic phase obtained was fractionated, washed with water, and then dried over anhydrous magnesium sulfate. The solution obtained was concentrated under reduced pressure, and the residue obtained was purified with a fractional operation by means of column chromatography using toluene as the eluent and silica gel as the stationary phase powder. The product was further purified by means of recrystallization from ethanol and dried, giving 18.8 g of ethyl 4-ethoxy-2,3-difluoro-4'-biphenylbenzoate (3). The yield based on the compound (1) was 67.9%.
2'-(carboxymethyl-carbamoyl)-5'-methoxy-biphenyl-4-carboxylic acid ethyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
71%
With sodium acetate; palladium diacetate; In dimethyl sulfoxide; at 120℃; for 24h;Schlenk technique;
General procedure: A mixture of benzoyl aminoacetic acid 1a (90 mg, 0.5 mmol), 4-iodo-toluene 2a (218 mg, 1.0 mmol), Pd(OAc)2(11 mg, 0.05 mmol), anhydrous NaOAc (82 mg, 1.0 mmol), and DMSO (2 mL) wasplaced in a 25 mL Schlenk tube with a rubber plug in air. The tube was heatedat 120 for 24 h. The reaction mixture was cooled, diluted with alcohol, filtered through Celite, and concentrated in vacuo. Theresidue was purified by silica gel column chromatographywith ethyl acetate/ acetic acid (v:v = 80:1) to afford the desired product 3a (120 mg, 89percent).
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