6-chloro-3,4-dihydro-2H-naphthalen-1-one

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: 2-amino-1-cyano-benzene (5.0 g, 42.3 mmol), 6-chloro-3, 4-dihydro-[2H]-napthalen-1-one (Organon Laboratories) (8.8 g, 48.7 mmol) and boron trifluoride diethyl etherate (1M, 6.4 ml, 52.4 mmol) were treated according to the general procedure described herein to give the title compound.

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

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

Procedure: A mixture of 35.72 of the product from Step B and 50 ml of thionyl chloride was heated at reflux for 2 hours and then stirred at room temperature for 18 hours. After this time thionyl chloride was removed at reduced pressure and the product was dissolved in carbon tetrachloride and concentrated at reduced pressure. The residue was dissolved in 150 ml of dichloroethane cooled to 0° C. and 28 g of aluminum chloride was added portionwise over about 1 hr in approximately 3 g portions. After stirring for 3 hrs the reaction was poured over a mixture of ice/1N HCl and extracted three times with methylene chloride. The organic extracts were dried over magnesium sulfate and concentrated to approximately 30 g of a brown oil. Chromatography on silica gel with 10% ethyl acetate/hexane afforded 17.83 g of 6-chloro-3,4-dihydro-1(2H)-naphthalenone as a brown oil. 1H NMR was consistent with the structure. was heated at reflux for 2 hours After this time thionyl chloride was removed at reduced pressure the product was dissolved in carbon tetrachloride concentrated at reduced pressure The residue was dissolved in 150 ml of dichloroethane cooled to 0° C. 28 g of aluminum chloride was added portionwise over about 1 hr in approximately 3 g portions After stirring for 3 hrs the reaction was poured over a mixture of ice/1N HCl extracted three times with methylene chloride The organic extracts were dried over magnesium sulfate concentrated to approximately 30 g of a brown oil

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

Procedure: A mixture of 35.72 of the product from Step B and 50 ml of thionyl chloride was heated at reflux for 2 hours and then stirred at room temperature for 18 hrs. After this time thionyl chloride was removed at reduced pressure and the product was dissolved in carbon tetrachloride and concentrated at reduced pressure. The residue was dissolved in 150 ml of dichloroethane cooled to 0° C. and 28 g of aluminum chloride was added portionwise over about 1 hr in approximately 3 g portions. After stirring for 3 hrs the reaction was poured over a mixture of ice/1N HCl and extracted three times with methylene chloride. The organic extracts were dried over magnesium sulfate and concentrated to approximately 30 g of a brown oil. Chromatography on silica gel with 10% ethyl acetate/hexane afforded 17.83 g of 6-chloro-3,4-dihydro-1(2H)-naphthalenone as a brown oil. 1H NMR was consistent with the structure. was heated at reflux for 2 hours After this time thionyl chloride was removed at reduced pressure the product was dissolved in carbon tetrachloride concentrated at reduced pressure The residue was dissolved in 150 ml of dichloroethane cooled to 0° C. 28 g of aluminum chloride was added portionwise over about 1 hr in approximately 3 g portions After stirring for 3 hrs the reaction was poured over a mixture of ice/1N HCl extracted three times with methylene chloride The organic extracts were dried over magnesium sulfate concentrated to approximately 30 g of a brown oil

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

Procedure: A mixture of 35.72 of the product from Step B and 50 ml of thionyl chloride was heated at reflux for 2 hours and then stirred at room temperature for 18 hrs. After this time thionyl chloride was removed at reduced pressure and the product was dissolved in carbon tetrachloride and concentrated at reduced pressure. The residue was dissolved in 150 ml of dichloroethane cooled to 0° C. and 28 g of aluminum chloride was added portionwise over about 1 hr in approximately 3 g portions. After stirring for 3 hrs the reaction was poured over a mixture of ice/1N HCl and extracted three times with methylene chloride. The organic extracts were dried over magnesium sulfate and concentrated to approximately 30 g of a brown oil. Chromatography on silica gel with 10% ethyl acetate/hexane afforded 17.83 g of 6-chloro-3,4-dihydro-1(2H)-naphthalenone as a brown oil. 1H NMR was consistent with the structure. was heated at reflux for 2 hours After this time thionyl chloride was removed at reduced pressure the product was dissolved in carbon tetrachloride concentrated at reduced pressure The residue was dissolved in 150 ml of dichloroethane cooled to 0° C. 28 g of aluminum chloride was added portionwise over about 1 hr in approximately 3 g portions After stirring for 3 hrs the reaction was poured over a mixture of ice/1N HCl extracted three times with methylene chloride The organic extracts were dried over magnesium sulfate concentrated to approximately 30 g of a brown oil

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

Procedure: 2-amino-1-cyano-benzene (5.0 g, 42.3 mmol), 6-chloro-3, 4-dihydro-[2H]-napthalen-1-one (Organon Laboratories) (8.8 g, 48.7 mmol) and boron trifluoride diethyl etherate (1M, 6.4 ml, 52.4 mmol) were treated according to the general procedure described herein to give the title compound.

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

Procedure: 2-amino-1-cyano-benzene (5.0 g, 42.3 mmol), 6-chloro-3, 4-dihydro-[2H]-napthalen-1-one (Organon Laboratories) (8.8 g, 48.7 mmol) and boron trifluoride diethyl etherate (1M, 6.4 ml, 52.4 mmol) were treated according to the general procedure described herein to give the title compound.

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

Procedure: A mixture of 35.72 of the product from Step B and 50 ml of thionyl chloride was heated at reflux for 2 hours and then stirred at room temperature for 18 hours. After this time thionyl chloride was removed at reduced pressure and the product was dissolved in carbon tetrachloride and concentrated at reduced pressure. The residue was dissolved in 150 ml of dichloroethane cooled to 0° C. and 28 g of aluminum chloride was added portionwise over about 1 hr in approximately 3 g portions. After stirring for 3 hrs the reaction was poured over a mixture of ice/1N HCl and extracted three times with methylene chloride. The organic extracts were dried over magnesium sulfate and concentrated to approximately 30 g of a brown oil. Chromatography on silica gel with 10% ethyl acetate/hexane afforded 17.83 g of 6-chloro-3,4-dihydro-1(2H)-naphthalenone as a brown oil. 1H NMR was consistent with the structure. was heated at reflux for 2 hours After this time thionyl chloride was removed at reduced pressure the product was dissolved in carbon tetrachloride concentrated at reduced pressure The residue was dissolved in 150 ml of dichloroethane cooled to 0° C. 28 g of aluminum chloride was added portionwise over about 1 hr in approximately 3 g portions After stirring for 3 hrs the reaction was poured over a mixture of ice/1N HCl extracted three times with methylene chloride The organic extracts were dried over magnesium sulfate concentrated to approximately 30 g of a brown oil

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

Procedure: 5 g of 6-chloro-1-tetralone are reacted with 4.4 g of bromine in ethyl acetate analogously to the instructions indicated in Example 29 (a). After distilling off the solvent under reduced pressure, 2-bromo-6-chloro-1-tetralone is obtained as an amorphous residue, which is used without further purification. After distilling off the solvent under reduced pressure

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

Procedure: 5 g of 6-chloro-1-tetralone are reacted with 4.4 g of bromine in ethyl acetate analogously to the instructions indicated in Example 29 (a). After distilling off the solvent under reduced pressure, 2-bromo-6-chloro-1-tetralone is obtained as an amorphous residue, which is used without further purification. After distilling off the solvent under reduced pressure