3-(4-bromo-2-methoxyphenyl)cyclobutan-1-one

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

Procedure: Sodium borohydride (0.25 g, 6.75 mmol) was added to a solution of 3-(4-bromo-2-methoxyphenyl)cyclobutanone (1.87 g, 7.3 mmol) in tetrahydrofuran (70 mL) at 0° C., the reaction was stirred room temperature 1 hr, extracted with 1:1 solution of ethyl acetate in heptane, the organic layers was washed with brine (50 mL), dried over sodium sulfate, and concentrated to give the title compound (1.34 g, 77.18%). extracted with 1:1 solution of ethyl acetate in heptane the organic layers was washed with brine (50 mL) dried over sodium sulfate concentrated

Conditions: temp:23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 50 mL round-bottom flask equipped with a reflux condenser is placed 3-(4-bromo-2-methoxyphenyl)-2,2-dichlorocyclobutanone (300 mg, 1.08 mmol) and activated zinc (280 mg, 4.30 mmol), in a saturated methanolic ammonium chloride solution (2 ml), the suspension is refluxed for 6 hr, then cooled to 23° C. and filtered through celite and rinsed with petroleum ether (10 mL), and organics are rinsed with water (10 mL), sat sodium bicarbonate (10 mL) and brine (10 ml), dried over sodium sulfate and concentrated under reduced pressure, the crude material was purified by silica gel chromatography to give the title compound (200 mg, 85%). In a 50 mL round-bottom flask equipped with a reflux condenser filtered through celite rinsed with petroleum ether (10 mL) organics are rinsed with water (10 mL) dried over sodium sulfate concentrated under reduced pressure the crude material was purified by silica gel chromatography

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

Procedure: Sodium borohydride (0.25 g, 6.75 mmol) was added to a solution of 3-(4-bromo-2-methoxyphenyl)cyclobutanone (1.87 g, 7.3 mmol) in tetrahydrofuran (70 mL) at 0° C., the reaction was stirred room temperature 1 hr, extracted with 1:1 solution of ethyl acetate in heptane, the organic layers was washed with brine (50 mL), dried over sodium sulfate, and concentrated to give the title compound (1.34 g, 77.18%). extracted with 1:1 solution of ethyl acetate in heptane the organic layers was washed with brine (50 mL) dried over sodium sulfate concentrated

Conditions: temp:23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 50 mL round-bottom flask equipped with a reflux condenser is placed 3-(4-bromo-2-methoxyphenyl)-2,2-dichlorocyclobutanone (300 mg, 1.08 mmol) and activated zinc (280 mg, 4.30 mmol), in a saturated methanolic ammonium chloride solution (2 ml), the suspension is refluxed for 6 hr, then cooled to 23° C. and filtered through celite and rinsed with petroleum ether (10 mL), and organics are rinsed with water (10 mL), sat sodium bicarbonate (10 mL) and brine (10 ml), dried over sodium sulfate and concentrated under reduced pressure, the crude material was purified by silica gel chromatography to give the title compound (200 mg, 85%). In a 50 mL round-bottom flask equipped with a reflux condenser filtered through celite rinsed with petroleum ether (10 mL) organics are rinsed with water (10 mL) dried over sodium sulfate concentrated under reduced pressure the crude material was purified by silica gel chromatography

Conditions: temp:23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 50 mL round-bottom flask equipped with a reflux condenser is placed 3-(4-bromo-2-methoxyphenyl)-2,2-dichlorocyclobutanone (300 mg, 1.08 mmol) and activated zinc (280 mg, 4.30 mmol), in a saturated methanolic ammonium chloride solution (2 ml), the suspension is refluxed for 6 hr, then cooled to 23° C. and filtered through celite and rinsed with petroleum ether (10 mL), and organics are rinsed with water (10 mL), sat sodium bicarbonate (10 mL) and brine (10 ml), dried over sodium sulfate and concentrated under reduced pressure, the crude material was purified by silica gel chromatography to give the title compound (200 mg, 85%). In a 50 mL round-bottom flask equipped with a reflux condenser filtered through celite rinsed with petroleum ether (10 mL) organics are rinsed with water (10 mL) dried over sodium sulfate concentrated under reduced pressure the crude material was purified by silica gel chromatography

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

Procedure: Sodium borohydride (0.25 g, 6.75 mmol) was added to a solution of 3-(4-bromo-2-methoxyphenyl)cyclobutanone (1.87 g, 7.3 mmol) in tetrahydrofuran (70 mL) at 0° C., the reaction was stirred room temperature 1 hr, extracted with 1:1 solution of ethyl acetate in heptane, the organic layers was washed with brine (50 mL), dried over sodium sulfate, and concentrated to give the title compound (1.34 g, 77.18%). extracted with 1:1 solution of ethyl acetate in heptane the organic layers was washed with brine (50 mL) dried over sodium sulfate concentrated

Conditions: temp:23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 50 mL round-bottom flask equipped with a reflux condenser is placed 3-(4-bromo-2-methoxyphenyl)-2,2-dichlorocyclobutanone (300 mg, 1.08 mmol) and activated zinc (280 mg, 4.30 mmol), in a saturated methanolic ammonium chloride solution (2 ml), the suspension is refluxed for 6 hr, then cooled to 23° C. and filtered through celite and rinsed with petroleum ether (10 mL), and organics are rinsed with water (10 mL), sat sodium bicarbonate (10 mL) and brine (10 ml), dried over sodium sulfate and concentrated under reduced pressure, the crude material was purified by silica gel chromatography to give the title compound (200 mg, 85%). In a 50 mL round-bottom flask equipped with a reflux condenser filtered through celite rinsed with petroleum ether (10 mL) organics are rinsed with water (10 mL) dried over sodium sulfate concentrated under reduced pressure the crude material was purified by silica gel chromatography

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

Procedure: Sodium borohydride (0.25 g, 6.75 mmol) was added to a solution of 3-(4-bromo-2-methoxyphenyl)cyclobutanone (1.87 g, 7.3 mmol) in tetrahydrofuran (70 mL) at 0° C., the reaction was stirred room temperature 1 hr, extracted with 1:1 solution of ethyl acetate in heptane, the organic layers was washed with brine (50 mL), dried over sodium sulfate, and concentrated to give the title compound (1.34 g, 77.18%). extracted with 1:1 solution of ethyl acetate in heptane the organic layers was washed with brine (50 mL) dried over sodium sulfate concentrated

Conditions: temp:23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 50 mL round-bottom flask equipped with a reflux condenser is placed 3-(4-bromo-2-methoxyphenyl)-2,2-dichlorocyclobutanone (300 mg, 1.08 mmol) and activated zinc (280 mg, 4.30 mmol), in a saturated methanolic ammonium chloride solution (2 ml), the suspension is refluxed for 6 hr, then cooled to 23° C. and filtered through celite and rinsed with petroleum ether (10 mL), and organics are rinsed with water (10 mL), sat sodium bicarbonate (10 mL) and brine (10 ml), dried over sodium sulfate and concentrated under reduced pressure, the crude material was purified by silica gel chromatography to give the title compound (200 mg, 85%). In a 50 mL round-bottom flask equipped with a reflux condenser filtered through celite rinsed with petroleum ether (10 mL) organics are rinsed with water (10 mL) dried over sodium sulfate concentrated under reduced pressure the crude material was purified by silica gel chromatography

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

Procedure: Sodium borohydride (0.25 g, 6.75 mmol) was added to a solution of 3-(4-bromo-2-methoxyphenyl)cyclobutanone (1.87 g, 7.3 mmol) in tetrahydrofuran (70 mL) at 0° C., the reaction was stirred room temperature 1 hr, extracted with 1:1 solution of ethyl acetate in heptane, the organic layers was washed with brine (50 mL), dried over sodium sulfate, and concentrated to give the title compound (1.34 g, 77.18%). extracted with 1:1 solution of ethyl acetate in heptane the organic layers was washed with brine (50 mL) dried over sodium sulfate concentrated

Conditions: temp:23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 50 mL round-bottom flask equipped with a reflux condenser is placed 3-(4-bromo-2-methoxyphenyl)-2,2-dichlorocyclobutanone (300 mg, 1.08 mmol) and activated zinc (280 mg, 4.30 mmol), in a saturated methanolic ammonium chloride solution (2 ml), the suspension is refluxed for 6 hr, then cooled to 23° C. and filtered through celite and rinsed with petroleum ether (10 mL), and organics are rinsed with water (10 mL), sat sodium bicarbonate (10 mL) and brine (10 ml), dried over sodium sulfate and concentrated under reduced pressure, the crude material was purified by silica gel chromatography to give the title compound (200 mg, 85%). In a 50 mL round-bottom flask equipped with a reflux condenser filtered through celite rinsed with petroleum ether (10 mL) organics are rinsed with water (10 mL) dried over sodium sulfate concentrated under reduced pressure the crude material was purified by silica gel chromatography