6-chloro-7-fluoro-3,4-dihydro-2H-isoquinolin-1-one

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

Procedure: A mixture of 6-chloro-7-fluoro-1,2,3,4-tetrahydro-isoquinoline (130 mg, 0.7 mmol), potassium bromide (83.5 mg, 0.7 mmol) and iodoso benzene (0.46 g, 2.1 mmol) in water (4 mL) was stirred at room temperature overnight. The mixture was then extracted with EtOAc and the organic layer was dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product. Flash column chromatography separation (silica gel, 12 g, 30% EtOAc in hexane) then afforded the tile compound (58 mg, 41%) as a white solid. The mixture was then extracted with EtOAc the organic layer was dried over anhy Na2SO4, filtered concentrated in vacuo to give a crude product Flash column chromatography separation (silica gel, 12 g, 30% EtOAc in hexane)

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

Procedure: A mixture of 6-chloro-7-fluoro-1,2,3,4-tetrahydro-isoquinoline (130 mg, 0.7 mmol), potassium bromide (83.5 mg, 0.7 mmol) and iodoso benzene (0.46 g, 2.1 mmol) in water (4 mL) was stirred at room temperature overnight. The mixture was then extracted with EtOAc and the organic layer was dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product. Flash column chromatography separation (silica gel, 12 g, 30% EtOAc in hexane) then afforded the tile compound (58 mg, 41%) as a white solid. The mixture was then extracted with EtOAc the organic layer was dried over anhy Na2SO4, filtered concentrated in vacuo to give a crude product Flash column chromatography separation (silica gel, 12 g, 30% EtOAc in hexane)