tetrabutylazanium;fluoride;hydrofluoride

Conditions: temp:25.01; pressure:0.00; stir:

Conditions: temp:25.01; pressure:0.00; stir:

Conditions: temp:25.01; pressure:0.00; stir:

Conditions: temp:25.01; pressure:0.00; stir:

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

Procedure: To a solution of 1-[2-(benzyloxy)phenyl]-2-bromoethanone (2.59 g, 8.5 mmol) and pyridine (1.37 mL, 17 mmol) in THF was added tetrabutylammonium hydrogen difluoride (4.78 g, 17 mmol). The reaction mixture was stirred under reflux for 22 hrs. The mixture was diluted with ether (250 mL), then washed with 1N aqueous hydrochloric acid (100 mL) and brine (100 mL), successively. The organic phase was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (hexane/ethyl acetate, 4:1) to give 1-[2-(benzyloxy)phenyl]-2-fluoroethanone (688 mg, yield; 33%). under reflux for 22 hrs washed with 1N aqueous hydrochloric acid (100 mL) and brine (100 mL) The organic phase was dried over Na2SO4 filtered concentrated under reduced pressure The crude product was purified by column chromatography on silica gel (hexane/ethyl acetate, 4:1)

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

Procedure: To a solution of 1-[2-(benzyloxy)phenyl]-2-bromoethanone (2.59 g, 8.5 mmol) and pyridine (1.37 mL, 17 mmol) in THF was added tetrabutylammonium hydrogen difluoride (4.78 g, 17 mmol). The reaction mixture was stirred under reflux for 22 hrs. The mixture was diluted with ether (250 mL), then washed with 1N aqueous hydrochloric acid (100 mL) and brine (100 mL), successively. The organic phase was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (hexane/ethyl acetate, 4:1) to give 1-[2-(benzyloxy)phenyl]-2-fluoroethanone (688 mg, yield; 33%). under reflux for 22 hrs washed with 1N aqueous hydrochloric acid (100 mL) and brine (100 mL) The organic phase was dried over Na2SO4 filtered concentrated under reduced pressure The crude product was purified by column chromatography on silica gel (hexane/ethyl acetate, 4:1)

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

Procedure: To a solution of 1-[2-(benzyloxy) phenyl]-2-bromoethanone (2.59 g, 8.5 mmol) and pyridine (1.37 mL, 17 mmol) in THF was added tetrabutylammonium hydrogen difluoride (4.78 g, 17 mmol). The reaction mixture was stirred under reflux for 22 hrs. The mixture was diluted with ether (250 mL), then washed with 1N aqueous hydrochloric acid (100 mL) and brine (100 mL), successively. The organic phase was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (hexane/ethyl acetate, 4:1) to give 1-[2-(benzyloxy)phenyl]-2-fluoroethanone (688 mg, yield; 33%). under reflux for 22 hrs washed with 1N aqueous hydrochloric acid (100 mL) and brine (100 mL) The organic phase was dried over Na2SO4 filtered concentrated under reduced pressure The crude product was purified by column chromatography on silica gel (hexane/ethyl acetate, 4:1)

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

Procedure: To a solution of 1-[2-(benzyloxy)phenyl]-2-bromoethanone (2.59 g, 8.5 mmol) and pyridine (1.37 mL, 17 mmol) in THF was added tetrabutylammonium hydrogen difluoride (4.78 g, 17 mmol). The reaction mixture was stirred under reflux for 22 hrs. The mixture was diluted with ether (250 mL), then washed with 1N aqueous hydrochloric acid (100 mL) and brine (100 mL), successively. The organic phase was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (hexane/ethyl acetate, 4:1) to give 1-[2-(benzyloxy)phenyl]-2-fluoroethanone (688 mg, yield; 33%). under reflux for 22 hrs washed with 1N aqueous hydrochloric acid (100 mL) and brine (100 mL) The organic phase was dried over Na2SO4 filtered concentrated under reduced pressure The crude product was purified by column chromatography on silica gel (hexane/ethyl acetate, 4:1)

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

Procedure: To a solution of 1-[2-(benzyloxy)phenyl]-2-bromoethanone (2.59 g, 8.5 mmol) and pyridine (1.37 mL, 17 mmol) in THF was added tetrabutylammonium hydrogen difluoride (4.78 g, 17 mmol). The reaction mixture was stirred under reflux for 22 hrs. The mixture was diluted with ether (250 mL), then washed with 1N aqueous hydrochloric acid (100 mL) and brine (100 mL), successively. The organic phase was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (hexane/ethyl acetate, 4:1) to give 1-[2-(benzyloxy)phenyl]-2-fluoroethanone (688 mg, yield; 33%). [Starting Compound 1C] under reflux for 22 hrs washed with 1N aqueous hydrochloric acid (100 mL) and brine (100 mL) The organic phase was dried over Na2SO4 filtered concentrated under reduced pressure The crude product was purified by column chromatography on silica gel (hexane/ethyl acetate, 4:1)

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

Procedure: To an ice-cold suspension of diethylaminodifluorosulfinium tetrafluoroborate (458 mg, 2.0 mmol) and tetrabutylammonium hydrogen difluoride (463 mg, 2.0 mmol) in dichloromethane (3.0 mL) under nitrogen is added 4-carboethoxycyclohexanone (159 μl, 1.0 mmol). The reaction mixture is allowed to warm to room temperature and stirred for 4 h. The reaction mixture is quenched at room temperature with a saturated aqueous ammonium chloride solution, stirred for 15 min, and the resulting mixture is extracted twice using dichloromethane. The organic phases are combined, dried over magnesium sulfate, filtered and concentrated. The crude product is passed through a pad of silica gel using pentane to provide 1-carboethoxy-4,4-difluorocyclohexane (130 mg, 68%) as a clear oil. The reaction mixture is quenched at room temperature with a saturated aqueous ammonium chloride solution stirred for 15 min the resulting mixture is extracted twice using dichloromethane dried over magnesium sulfate filtered concentrated

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

Procedure: To a solution of 1-[2-(benzyloxy)phenyl]-2-bromoethanone (2.59 g, 8.5 mmol) and pyridine (1.37 mL, 17 mmol) in THF was added tetrabutylammonium hydrogen difluoride (4.78 g, 17 mmol). The reaction mixture was stirred under reflux for 22 hrs. The mixture was diluted with ether (250 mL), then washed with 1N aqueous hydrochloric acid (100 mL) and brine (100 mL), successively. The organic phase was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (hexane/ethyl acetate, 4:1) to give 1-[2-(benzyloxy)phenyl]-2-fluoroethanone (688 mg, yield; 33%). under reflux for 22 hrs washed with 1N aqueous hydrochloric acid (100 mL) and brine (100 mL) The organic phase was dried over Na2SO4 filtered concentrated under reduced pressure The crude product was purified by column chromatography on silica gel (hexane/ethyl acetate, 4:1)