1-benzyl-2-bromobenzene

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

Procedure: 26.25 ml of 2.4 molar solution of n-butyllithium in n-hexane is added dropwise with stirring at -50° to -40° C. under dry nitrogen to a solution of 10.87 g of 2-bromodiphenylmethane in 25 ml of dry THF. The mixture is stirred at -50° to -40° C. for one hour after addition is completed. A solution of 6.30 g of 1,4-dioxaspiro(4.5)decan-8-one in 20 ml of dry THF is added dropwise at -50° to -40° C. This mixture is stirred overnight (16 hours) at -70° C. to +10° C., and quenched with 50 ml of water. The organic phase is diluted with 100 ml of ether and washed three times with 50 ml portions of water. The aqueous phase and the washing water are extracted with 100 ml of CH2Cl2, which is washed twice with 50 ml portions of water. The combined organic phases are dried over Na2SO4 and evaporated to an oil. This oil is treated with ether/hexane (20 ml/50 ml) mixture to give 6.0 g (45.8%) yield of crystalline product which is recrystallized from ether/hexane (10 ml/40 ml) to provide 5.53 g (42.2% yield) of 8-[2-(phenylmethyl)phenyl]-1,4-dioxaspiro(4.5)decan-8-ol, m.p. 97°-98° C. after addition This mixture is stirred overnight (16 hours) at -70° C. to +10° C. quenched with 50 ml of water The organic phase is diluted with 100 ml of ether washed three times with 50 ml portions of water The aqueous phase and the washing water are extracted with 100 ml of CH2Cl2, which is washed twice with 50 ml portions of water The combined organic phases are dried over Na2SO4 evaporated to an oil This oil is treated with ether/hexane (20 ml/50 ml) mixture to give 6.0 g (45.8%) yield of crystalline product which is recrystallized from ether/hexane (10 ml/40 ml)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 24.7 g of 2-bromodiphenylmethane and 100 ml of dry tetrahydrofuran (THF, hereinafter) is added 55 ml of 2.4 molar solution of n-butyllithium in hexane dropwise with stirring at -40° to 50° C. under a dry nitrogen atmosphere. The resultant solution is stirred one hour after addition of the n-butyllithium is completed. A solution of 15.5 g 4-dimethylaminocyclohexanone in 50 ml of dry THF is added dropwise with stirring while maintaining the temperature below -40° C. The resultant solution is stirred at -40°0 to -50° C. for two hours after addition of the ketone is completed and further stirred under N2 atmosphere overnight (16 hours) at room temperature. The solution is cooled to 0° C. and 350 ml of water and 400 ml of hexane are added thereto. The aqueous phase of the resultant mixture is removed and the product crystallized out of the organic phase. After filtration (washing the filter cake with hexane) the organic phase is washed three times with 100°ml portions of water and cooled overnight. A second crop is obtained, combined with the first crop and recrystallized from 50 ml of toluene to yield 9.46 g (30.6% yield) of 1-[2-(phenylmethyl)phenyl]-4-dimethylaminocyclohexanol, m.p. 140°-141° C. with stirring while maintaining the temperature below -40° C further stirred under N2 atmosphere overnight (16 hours) at room temperature The aqueous phase of the resultant mixture is removed the product crystallized out of the organic phase After filtration ( washing the filter cake with hexane) the organic phase is washed three times with 100°ml portions of water cooled overnight A second crop is obtained recrystallized from 50 ml of toluene