Ethyl 2-(4-iodophenyl)acetate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a sealed tube were added 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (2.2 g, 10 mmol), ethyl 2-(4-iodophenyl)acetate 26-1 (2.9 g, 10 mmol), Pd(PPh3)4 (0.231 g, 0.2 mmol), toluene (30 mL), ethanol (10 mL) and 2M Na2CO3 (10 mL). The reaction mixture was flushed with nitrogen and stirred at 90° C. for 10 hours. After cooled down to room temperature, the reaction mixture was diluted into 200 mL ethyl acetate and washed with saturated sodium bicarbonate solution and then brine. The organic phase was dried over Na2SO4 and then taken to dryness by rotary evaporation. The crude product was purified by silica gel flash chromatography, eluted with 50% ethyl acetate in hexane to give ethyl 2-(4-(2-methylpyridin-4-yl)phenyl)acetate 26-2 as an oil. MS m/z 256.1 (M+1). The reaction mixture was flushed with nitrogen After cooled down to room temperature the reaction mixture was diluted into 200 mL ethyl acetate washed with saturated sodium bicarbonate solution The organic phase was dried over Na2SO4 taken to dryness by rotary evaporation The crude product was purified by silica gel flash chromatography eluted with 50% ethyl acetate in hexane

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a sealed tube were added 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (2.2 g, 10 mmol), ethyl 2-(4-iodophenyl)acetate 26-1 (2.9 g, 10 mmol), Pd(PPh3)4 (0.231 g, 0.2 mmol), toluene (30 mL), ethanol (10 mL) and 2M Na2CO3 (10 mL). The reaction mixture was flushed with nitrogen and stirred at 90° C. for 10 hours. After cooled down to room temperature, the reaction mixture was diluted into 200 mL ethyl acetate and washed with saturated sodium bicarbonate solution and then brine. The organic phase was dried over Na2SO4 and then taken to dryness by rotary evaporation. The crude product was purified by silica gel flash chromatography, eluted with 50% ethyl acetate in hexane to give ethyl 2-(4-(2-methylpyridin-4-yl)phenyl)acetate 26-2 as an oil. MS m/z 256.1 (M+1). The reaction mixture was flushed with nitrogen After cooled down to room temperature the reaction mixture was diluted into 200 mL ethyl acetate washed with saturated sodium bicarbonate solution The organic phase was dried over Na2SO4 taken to dryness by rotary evaporation The crude product was purified by silica gel flash chromatography eluted with 50% ethyl acetate in hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Iodophenylacetic acid (3 g), ethanol (20 mL) and conc. H2SO4 (5 mL) were refluxed overnight. Ca. 15 mL ethanol was then evaporated, the residue was extracted with dichloromethane (3×100 mL), the combined organic extracts were washed with sat. aq. NaHCO3, dried over Na2SO4 and evaporated in vacuo to afford 2.97 g (90%) of 121JP58 as a yellow oil. 15 mL ethanol was then evaporated the residue was extracted with dichloromethane (3×100 mL) the combined organic extracts were washed with sat. aq. NaHCO3 dried over Na2SO4 evaporated in vacuo

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a sealed tube were added 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (2.2 g, 10 mmol), ethyl 2-(4-iodophenyl)acetate 26-1 (2.9 g, 10 mmol), Pd(PPh3)4 (0.231 g, 0.2 mmol), toluene (30 mL), ethanol (10 mL) and 2M Na2CO3 (10 mL). The reaction mixture was flushed with nitrogen and stirred at 90° C. for 10 hours. After cooled down to room temperature, the reaction mixture was diluted into 200 mL ethyl acetate and washed with saturated sodium bicarbonate solution and then brine. The organic phase was dried over Na2SO4 and then taken to dryness by rotary evaporation. The crude product was purified by silica gel flash chromatography, eluted with 50% ethyl acetate in hexane to give ethyl 2-(4-(2-methylpyridin-4-yl)phenyl)acetate 26-2 as an oil. MS m/z 256.1 (M+1). The reaction mixture was flushed with nitrogen After cooled down to room temperature the reaction mixture was diluted into 200 mL ethyl acetate washed with saturated sodium bicarbonate solution The organic phase was dried over Na2SO4 taken to dryness by rotary evaporation The crude product was purified by silica gel flash chromatography eluted with 50% ethyl acetate in hexane

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a sealed tube were added 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (2.2 g, 10 mmol), ethyl 2-(4-iodophenyl)acetate 26-1 (2.9 g, 10 mmol), Pd(PPh3)4 (0.231 g, 0.2 mmol), toluene (30 mL), ethanol (10 mL) and 2M Na2CO3 (10 mL). The reaction mixture was flushed with nitrogen and stirred at 90° C. for 10 hours. After cooled down to room temperature, the reaction mixture was diluted into 200 mL ethyl acetate and washed with saturated sodium bicarbonate solution and then brine. The organic phase was dried over Na2SO4 and then taken to dryness by rotary evaporation. The crude product was purified by silica gel flash chromatography, eluted with 50% ethyl acetate in hexane to give ethyl 2-(4-(2-methylpyridin-4-yl)phenyl)acetate 26-2 as an oil. MS m/z 256.1 (M+1). The reaction mixture was flushed with nitrogen After cooled down to room temperature the reaction mixture was diluted into 200 mL ethyl acetate washed with saturated sodium bicarbonate solution The organic phase was dried over Na2SO4 taken to dryness by rotary evaporation The crude product was purified by silica gel flash chromatography eluted with 50% ethyl acetate in hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Iodophenylacetic acid (3 g), ethanol (20 mL) and conc. H2SO4 (5 mL) were refluxed overnight. Ca. 15 mL ethanol was then evaporated, the residue was extracted with dichloromethane (3×100 mL), the combined organic extracts were washed with sat. aq. NaHCO3, dried over Na2SO4 and evaporated in vacuo to afford 2.97 g (90%) of 121JP58 as a yellow oil. 15 mL ethanol was then evaporated the residue was extracted with dichloromethane (3×100 mL) the combined organic extracts were washed with sat. aq. NaHCO3 dried over Na2SO4 evaporated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Iodophenylacetic acid (3 g), ethanol (20 mL) and conc. H2SO4 (5 mL) were refluxed overnight. Ca. 15 mL ethanol was then evaporated, the residue was extracted with dichloromethane (3×100 mL), the combined organic extracts were washed with sat. aq. NaHCO3, dried over Na2SO4 and evaporated in vacuo to afford 2.97 g (90%) of 121JP58 as a yellow oil. 15 mL ethanol was then evaporated the residue was extracted with dichloromethane (3×100 mL) the combined organic extracts were washed with sat. aq. NaHCO3 dried over Na2SO4 evaporated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a manner similar to that of Example 1(h), by reaction of 543 mg (3.6 mmol) of 3-methoxymethoxyphenylboronic acid with 700 mg (2.4 mmol) of ethyl 4-iodophenylacetate, 630 mg (68%) of the expected ethyl ester are obtained. are obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In accordance with Example 11-(1), but using ethyl 4-iodophenylacetate instead of 4-bromobenzyl bromide, and (4-bromophenyl)boronic acid instead of [3-(hydroxymethyl)phenyl]boronic acid, ethyl (4′-bromobiphenyl-4-yl)acetate (yield 71%) was afforded as a white solid.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Iodophenylacetic acid (3 g), ethanol (20 mL) and conc. H2SO4 (5 mL) were refluxed overnight. Ca. 15 mL ethanol was then evaporated, the residue was extracted with dichloromethane (3×100 mL), the combined organic extracts were washed with sat. aq. NaHCO3, dried over Na2SO4 and evaporated in vacuo to afford 2.97 g (90%) of 121JP58 as a yellow oil. 15 mL ethanol was then evaporated the residue was extracted with dichloromethane (3×100 mL) the combined organic extracts were washed with sat. aq. NaHCO3 dried over Na2SO4 evaporated in vacuo