1-(3-bromo-5-hydroxyphenyl)ethanone

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

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

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

Procedure: A similar procedure as described in Example 43, step 3 was used, starting from 4-[3-[6-bromo-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (2.36 g, 5.0 mmol), 1-(3-bromo-5-hydroxy-phenyl)-ethanone (965 mg, 4.48 mmol), and potassium carbonate (1.38 g, 10 mmol) to afford 4-[3-[6-(3-acetyl-5-bromo-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (2.15 g, 79%) as a colorless viscous oil: EI(+)-HRMS m/e calcd for C31H41BrO7 (M+Na)+ 627.1928. found 627.1925.

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 1-(3-bromo-5-iodo-phenyl)-ethanone (2.28 g, 7.0 mmol), sodium hydroxide (1.4 g, 35.1 mmol), and Cu2O (143 mg, 1.0 mmol) were added pyridine (20 mL) and water (40 mL) at room temperature. The resulting suspension was heated to 110° C. and stirred for 24 h. Then the reaction mixture was cooled to room temperature and diluted with 1N hydrochloric acid (200 mL). Then, the organic compound was extracted into ethyl acetate (3×100 mL) and the combined organic extracts were washed with 1N hydrochloric acid (200 mL) and brine solution (200 mL). The organic layers were dried over anhydrous magnesium sulfate and filtration of the drying agent and concentration of the solvent under vacuum gave the crude dark brown solid which was tried to dissolve in acetonitrile (50 mL) at reflux, but it did not dissolve completely. Then, it was diluted with ethyl acetate (˜10 mL) and hexanes (˜15 mL). The dark suspension was stored in the refrigerator. Only few solids were formed and they were coolected by filtration and washed with acetonitrile. Then, the mother liquor was removed under vacuum and the dark brown solids were now dissolved in acetonitrile (50 mL) at reflux and it was treated with charcoal to remove some color. It was then filtered and the solvent was removed under vacuum to afford reasonably pure 1-(3-bromo-5-hydroxy-phenyl)-ethanone (965 mg, 64%) as a brown solid: ES(−)-HRMS m/e calcd for C8H7BrO2 (M−H)− 212.9556. found 212.9556. Then the reaction mixture was cooled to room temperature Then, the organic compound was extracted into ethyl acetate (3×100 mL) the combined organic extracts were washed with 1N hydrochloric acid (200 mL) and brine solution (200 mL) The organic layers were dried over anhydrous magnesium sulfate and filtration of the drying agent and concentration of the solvent under vacuum gave the crude dark brown solid which at reflux it did not dissolve completely Only few solids were formed they were coolected by filtration washed with acetonitrile Then, the mother liquor was removed under vacuum the dark brown solids were now dissolved in acetonitrile (50 mL) at reflux it was treated with charcoal to remove some color It was then filtered the solvent was removed under vacuum

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

Procedure: A similar procedure as described in Example 43, step 3 was used, starting from 4-[3-[6-bromo-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (2.36 g, 5.0 mmol), 1-(3-bromo-5-hydroxy-phenyl)-ethanone (965 mg, 4.48 mmol), and potassium carbonate (1.38 g, 10 mmol) to afford 4-[3-[6-(3-acetyl-5-bromo-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (2.15 g, 79%) as a colorless viscous oil: EI(+)-HRMS m/e calcd for C31H41BrO7 (M+Na)+ 627.1928. found 627.1925.

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 1-(3-bromo-5-iodo-phenyl)-ethanone (2.28 g, 7.0 mmol), sodium hydroxide (1.4 g, 35.1 mmol), and Cu2O (143 mg, 1.0 mmol) were added pyridine (20 mL) and water (40 mL) at room temperature. The resulting suspension was heated to 110° C. and stirred for 24 h. Then the reaction mixture was cooled to room temperature and diluted with 1N hydrochloric acid (200 mL). Then, the organic compound was extracted into ethyl acetate (3×100 mL) and the combined organic extracts were washed with 1N hydrochloric acid (200 mL) and brine solution (200 mL). The organic layers were dried over anhydrous magnesium sulfate and filtration of the drying agent and concentration of the solvent under vacuum gave the crude dark brown solid which was tried to dissolve in acetonitrile (50 mL) at reflux, but it did not dissolve completely. Then, it was diluted with ethyl acetate (˜10 mL) and hexanes (˜15 mL). The dark suspension was stored in the refrigerator. Only few solids were formed and they were coolected by filtration and washed with acetonitrile. Then, the mother liquor was removed under vacuum and the dark brown solids were now dissolved in acetonitrile (50 mL) at reflux and it was treated with charcoal to remove some color. It was then filtered and the solvent was removed under vacuum to afford reasonably pure 1-(3-bromo-5-hydroxy-phenyl)-ethanone (965 mg, 64%) as a brown solid: ES(−)-HRMS m/e calcd for C8H7BrO2 (M−H)− 212.9556. found 212.9556. Then the reaction mixture was cooled to room temperature Then, the organic compound was extracted into ethyl acetate (3×100 mL) the combined organic extracts were washed with 1N hydrochloric acid (200 mL) and brine solution (200 mL) The organic layers were dried over anhydrous magnesium sulfate and filtration of the drying agent and concentration of the solvent under vacuum gave the crude dark brown solid which at reflux it did not dissolve completely Only few solids were formed they were coolected by filtration washed with acetonitrile Then, the mother liquor was removed under vacuum the dark brown solids were now dissolved in acetonitrile (50 mL) at reflux it was treated with charcoal to remove some color It was then filtered the solvent was removed under vacuum

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 1-(3-bromo-5-iodo-phenyl)-ethanone (2.28 g, 7.0 mmol), sodium hydroxide (1.4 g, 35.1 mmol), and Cu2O (143 mg, 1.0 mmol) were added pyridine (20 mL) and water (40 mL) at room temperature. The resulting suspension was heated to 110° C. and stirred for 24 h. Then the reaction mixture was cooled to room temperature and diluted with 1N hydrochloric acid (200 mL). Then, the organic compound was extracted into ethyl acetate (3×100 mL) and the combined organic extracts were washed with 1N hydrochloric acid (200 mL) and brine solution (200 mL). The organic layers were dried over anhydrous magnesium sulfate and filtration of the drying agent and concentration of the solvent under vacuum gave the crude dark brown solid which was tried to dissolve in acetonitrile (50 mL) at reflux, but it did not dissolve completely. Then, it was diluted with ethyl acetate (˜10 mL) and hexanes (˜15 mL). The dark suspension was stored in the refrigerator. Only few solids were formed and they were coolected by filtration and washed with acetonitrile. Then, the mother liquor was removed under vacuum and the dark brown solids were now dissolved in acetonitrile (50 mL) at reflux and it was treated with charcoal to remove some color. It was then filtered and the solvent was removed under vacuum to afford reasonably pure 1-(3-bromo-5-hydroxy-phenyl)-ethanone (965 mg, 64%) as a brown solid: ES(−)-HRMS m/e calcd for C8H7BrO2 (M−H)− 212.9556. found 212.9556. Then the reaction mixture was cooled to room temperature Then, the organic compound was extracted into ethyl acetate (3×100 mL) the combined organic extracts were washed with 1N hydrochloric acid (200 mL) and brine solution (200 mL) The organic layers were dried over anhydrous magnesium sulfate and filtration of the drying agent and concentration of the solvent under vacuum gave the crude dark brown solid which at reflux it did not dissolve completely Only few solids were formed they were coolected by filtration washed with acetonitrile Then, the mother liquor was removed under vacuum the dark brown solids were now dissolved in acetonitrile (50 mL) at reflux it was treated with charcoal to remove some color It was then filtered the solvent was removed under vacuum

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

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

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

Procedure: A similar procedure as described in Example 43, step 3 was used, starting from 4-[3-[6-bromo-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (2.36 g, 5.0 mmol), 1-(3-bromo-5-hydroxy-phenyl)-ethanone (965 mg, 4.48 mmol), and potassium carbonate (1.38 g, 10 mmol) to afford 4-[3-[6-(3-acetyl-5-bromo-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (2.15 g, 79%) as a colorless viscous oil: EI(+)-HRMS m/e calcd for C31H41BrO7 (M+Na)+ 627.1928. found 627.1925.

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 1-(3-bromo-5-iodo-phenyl)-ethanone (2.28 g, 7.0 mmol), sodium hydroxide (1.4 g, 35.1 mmol), and Cu2O (143 mg, 1.0 mmol) were added pyridine (20 mL) and water (40 mL) at room temperature. The resulting suspension was heated to 110° C. and stirred for 24 h. Then the reaction mixture was cooled to room temperature and diluted with 1N hydrochloric acid (200 mL). Then, the organic compound was extracted into ethyl acetate (3×100 mL) and the combined organic extracts were washed with 1N hydrochloric acid (200 mL) and brine solution (200 mL). The organic layers were dried over anhydrous magnesium sulfate and filtration of the drying agent and concentration of the solvent under vacuum gave the crude dark brown solid which was tried to dissolve in acetonitrile (50 mL) at reflux, but it did not dissolve completely. Then, it was diluted with ethyl acetate (˜10 mL) and hexanes (˜15 mL). The dark suspension was stored in the refrigerator. Only few solids were formed and they were coolected by filtration and washed with acetonitrile. Then, the mother liquor was removed under vacuum and the dark brown solids were now dissolved in acetonitrile (50 mL) at reflux and it was treated with charcoal to remove some color. It was then filtered and the solvent was removed under vacuum to afford reasonably pure 1-(3-bromo-5-hydroxy-phenyl)-ethanone (965 mg, 64%) as a brown solid: ES(−)-HRMS m/e calcd for C8H7BrO2 (M−H)− 212.9556. found 212.9556. Then the reaction mixture was cooled to room temperature Then, the organic compound was extracted into ethyl acetate (3×100 mL) the combined organic extracts were washed with 1N hydrochloric acid (200 mL) and brine solution (200 mL) The organic layers were dried over anhydrous magnesium sulfate and filtration of the drying agent and concentration of the solvent under vacuum gave the crude dark brown solid which at reflux it did not dissolve completely Only few solids were formed they were coolected by filtration washed with acetonitrile Then, the mother liquor was removed under vacuum the dark brown solids were now dissolved in acetonitrile (50 mL) at reflux it was treated with charcoal to remove some color It was then filtered the solvent was removed under vacuum