5-bromo-2-methyl-2,3-dihydroinden-1-one

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

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

Procedure: 5-Bromo-2-methyl-1-indanone (2.0 g) and cuprous cyanide (4.0 g) in quinoline (50 ml ) were stirred at 200° for 2 hours. The mixture was cooled, treated with chloroform (100 ml ) and filtered to remove copper salts. The filtrate was then washed with 6N hydrochloric acid (3×100 ml ) and evaporated to give the crude product as a brown gum. Crystallisation from ethanol-water gave 5-cyano-2-methyl-1-indanone (1.46 g, m.p. 90°-1°). The mixture was cooled filtered to remove copper salts The filtrate was then washed with 6N hydrochloric acid (3×100 ml ) evaporated to give the crude product as a brown gum Crystallisation from ethanol-water

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

Procedure: 5-Bromo-2-methyl-1-indanone (2.0 g) and cuprous cyanide (4.0 g) in quinoline (50 ml ) were stirred at 200° for 2 hours. The mixture was cooled, treated with chloroform (100 ml ) and filtered to remove copper salts. The filtrate was then washed with 6N hydrochloric acid (3×100 ml ) and evaporated to give the crude product as a brown gum. Crystallisation from ethanol-water gave 5-cyano-2-methyl-1-indanone (1.46 g, m.p. 90°-1°). The mixture was cooled filtered to remove copper salts The filtrate was then washed with 6N hydrochloric acid (3×100 ml ) evaporated to give the crude product as a brown gum Crystallisation from ethanol-water

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

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

Procedure: A solution of 5-bromo-1-indanone (3.75 g, 17.76 mmol) in 18 ml of anhydrous THF is brought to −20° C. under an atmosphere of argon and with magnetic stirring. A 1M solution of t-BuOK in THF (18 ml, 18 mmol) is added with a syringe and the stirring continued for 3 hours at ambient temperature. At 0° C., 10 ml of distilled water is added and the mixture then extracted with ether (4×75 ml), dried over MgSO4, filtered and evaporated to obtain a raw product that is incorporated onto silica and purified by flash chromatography on silica (eluent ether:petroleum ether=2:98 up to 5:95). In order of elution, one obtains 1.85 g of a yellowish oil, 2,2-dimethyl-5-bromo-1-indanone (yield=43%), 0.50 g of a white solid 2-methyl-5-bromo-1-indanone (yield=13%) and 1.20 g of a white solid (32%) the starting material, 5-bromo-1-indanone. is brought to −20° C. under an atmosphere of argon and with magnetic stirring the mixture then extracted with ether (4×75 ml) dried over MgSO4 filtered evaporated to obtain a raw product that purified by flash chromatography on silica (eluent ether:petroleum ether=2:98 up to 5:95) In order of elution, one

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

Procedure: 5-Bromo-2-methyl-1-indanone (2.0 g) and cuprous cyanide (4.0 g) in quinoline (50 ml ) were stirred at 200° for 2 hours. The mixture was cooled, treated with chloroform (100 ml ) and filtered to remove copper salts. The filtrate was then washed with 6N hydrochloric acid (3×100 ml ) and evaporated to give the crude product as a brown gum. Crystallisation from ethanol-water gave 5-cyano-2-methyl-1-indanone (1.46 g, m.p. 90°-1°). The mixture was cooled filtered to remove copper salts The filtrate was then washed with 6N hydrochloric acid (3×100 ml ) evaporated to give the crude product as a brown gum Crystallisation from ethanol-water