3-fluoro-6,7,8,9-tetrahydrobenzo[7]annulen-5-one

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

Procedure: To a stirred solution of 8-fluoro-1-benzosuberone (20.00 g, 112.2 mmol) in glacial acetic acid (125 ml) was added bromine (5.8 ml, 112.6 mmol) dropwise. Once the addition was complete, the solution was poured into water (400 ml) and extracted with EtOAc (500 ml). The extract was separated and washed with water (500 ml). The organic layer was dried over MgSO4, filtered and evaporated to yield 100% (28.9 g) of the desired product as a viscous oil: 1H-NMR (CDCl3) δ 2.00 (2H, m), 2.33 (2H, m), 2.84 (1H, m), 3.00 (1H, m), 4.83 (1H, m), 7.13 (2H, m), 7.29 (1H, dd). Once the addition extracted with EtOAc (500 ml) The extract was separated washed with water (500 ml) The organic layer was dried over MgSO4 filtered evaporated

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

Procedure: To a stirred solution of 8-fluoro-1-benzosuberone (20.00 g, 112.2 mmol) in glacial acetic acid (125 ml) was added bromine (5.8 ml, 112.6 mmol) dropwise. Once the addition was complete, the solution was poured into water (400 ml) and extracted with EtOAc (500 ml). The extract was separated and washed with water (500 ml). The organic layer was dried over MgSO4, filtered and evaporated to yield 100% (28.9 g) of the desired product as a viscous oil: 1H-NMR (CDCl3) δ 2.00 (2H, m), 2.33 (2H, m), 2.84 (1H, m), 3.00 (1H, m), 4.83 (1H, m), 7.13 (2H, m), 7.29 (1H, dd). Once the addition extracted with EtOAc (500 ml) The extract was separated washed with water (500 ml) The organic layer was dried over MgSO4 filtered evaporated

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

Procedure: 3-Fluoro-6,7,8,9-tetrahydro-benzocyclohepten-5-one (5.00 g, 28.00 mmol), NaBH3CN (12.50 g, 0.20 mol) and NH4OAc (65.00 g, 0.84 mol) in isopropanol were reacted according to the protocols as outlined in general procedure C to afford the title amine.

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

Procedure: 68.9 g of bromine are added dropwise to a solution of 73.1 g of 3-fluoro-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one in 700 ml of ether under ice-cooling during 1 hour. After the mixture is stirred for 1 hour, the reaction mixture is poured into water and the mixture is extracted with ether. The ether layer is washed, dried and evaporated to remove the solvent to obtain 106.8 g of 3-fluoro-6-bromo-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one as an oil. cooling during 1 hour the mixture is extracted with ether The ether layer is washed dried evaporated to remove the solvent

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

Procedure: To a stirred solution of 8-fluoro-1-benzosuberone (20.00 g, 112.2 mmol) in glacial acetic acid (125 ml) was added bromine (5.8 ml, 112.6 mmol) dropwise. Once the addition was complete, the solution was poured into water (400 ml) and extracted with EtOAc (500 ml). The extract was separated and washed with water (500 ml). The organic layer was dried over MgSO4, filtered and evaporated to yield 100% (28.9 g) of the desired product as a viscous oil: 1H-NMR (CDCl3) δ 2.00 (2H, m), 2.33 (2H, m), 2.84 (1H, m), 3.00 (1H, m), 4.83 (1H, m), 7.13 (2H, m), 7.29 (1H, dd). Once the addition extracted with EtOAc (500 ml) The extract was separated washed with water (500 ml) The organic layer was dried over MgSO4 filtered evaporated