propan-2-ylsulfonylbenzene

Conditions: temp:-40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of n-butyllithium in cyclohexanes (1.8M, 35.1 ml; 63.18 mmol) was added dropwise to a stirred solution of isopropyl phenyl sulphone (9.95 g, 54 mmol) in tetrahydrofuran (100 ml) keeping the temperature of the mixture below −60° C. The mixture was stirred for 30 min. and ethylene oxide was passed through the reaction mixture for 10 min. The mixture was warmed up to −40° C. for 30 min., then quenched with sat. aqueous NH4Cl and extracted into ethyl acetate. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified on silica gel (i-hexane:ethyl acetate) to give the title compound (12.3 g, 99%). the temperature of the mixture below −60° C quenched with sat. aqueous NH4Cl extracted into ethyl acetate The combined organic extracts were dried (Na2SO4) concentrated The residue was purified on silica gel (i-hexane:ethyl acetate)

Conditions: temp:-40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of n-butyllithium in cyclohexanes (1.8M, 35.1 ml; 63.18 mmol) was added dropwise to a stirred solution of isopropyl phenyl sulphone (9.95 g, 54 mmol) in tetrahydrofuran (100 ml) keeping the temperature of the mixture below −60° C. The mixture was stirred for 30 min. and ethylene oxide was passed through the reaction mixture for 10 min. The mixture was warmed up to −40° C. for 30 min., then quenched with sat. aqueous NH4Cl and extracted into ethyl acetate. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified on silica gel (i-hexane:ethyl acetate) to give the title compound (12.3 g, 99%). the temperature of the mixture below −60° C quenched with sat. aqueous NH4Cl extracted into ethyl acetate The combined organic extracts were dried (Na2SO4) concentrated The residue was purified on silica gel (i-hexane:ethyl acetate)

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

Procedure: A solution of n-butyllithium in cyclohexanes (1.82M, 18 ml, 32.8 mmol) was added dropwise to a stirred solution of phenyl i-propyl sulphone (5.55 g, 30.1 mmol) in tetrahydrofuran (60 ml) at −78° C. The mixture was stirred for 30 min. and 1,3-dibromopropane (6 ml, 58.7 mmol) was added via syringe over 30 seconds. The mixture was allowed to warm to 0° C. over 3 hours, then quenched with satd. aqueous NH4Cl and extracted into 1:1 mixture of i-hexane-diethyl ether. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified on silica (i-hexane-diethyl ether) to give the title product (5.7 g, 62%) as a white solid. quenched with satd aqueous NH4Cl and extracted into 1:1 mixture of i-hexane-diethyl ether The combined organic extracts were dried (Na2SO4) concentrated The residue was purified on silica (i-hexane-diethyl ether)

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

Procedure: A solution of n-butyllithium in cyclohexanes (1.82M, 18 ml, 32.8 mmol) was added dropwise to a stirred solution of phenyl i-propyl sulphone (5.55 g, 30.1 mmol) in tetrahydrofuran (60 ml) at −78° C. The mixture was stirred for 30 min. and 1,3-dibromopropane (6 ml, 58.7 mmol) was added via syringe over 30 seconds. The mixture was allowed to warm to 0° C. over 3 hours, then quenched with satd. aqueous NH4Cl and extracted into 1:1 mixture of i-hexane-diethyl ether. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified on silica (i-hexane-diethyl ether) to give the title product (5.7 g, 62%) as a white solid. quenched with satd aqueous NH4Cl and extracted into 1:1 mixture of i-hexane-diethyl ether The combined organic extracts were dried (Na2SO4) concentrated The residue was purified on silica (i-hexane-diethyl ether)

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

Procedure: A solution of n-butyllithium in cyclohexanes (1.82M, 18 ml, 32.8 mmol) was added dropwise to a stirred solution of phenyl i-propyl sulphone (5.55 g, 30.1 mmol) in tetrahydrofuran (60 ml) at −78° C. The mixture was stirred for 30 min. and 1,3-dibromopropane (6 ml, 58.7 mmol) was added via syringe over 30 seconds. The mixture was allowed to warm to 0° C. over 3 hours, then quenched with satd. aqueous NH4Cl and extracted into 1:1 mixture of i-hexane-diethyl ether. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified on silica (i-hexane-diethyl ether) to give the title product (5.7 g, 62%) as a white solid. quenched with satd aqueous NH4Cl and extracted into 1:1 mixture of i-hexane-diethyl ether The combined organic extracts were dried (Na2SO4) concentrated The residue was purified on silica (i-hexane-diethyl ether)

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

Procedure: To a solution of (propane-2-sulfonyl)-benzene (CAS#4238-09-9), which can be prepared as described in Cram, D. J. et al. Journal of the American Chemical Society, 1967, 89, 2072-2077, (1.18 g, 6.4 mmol) in THF (60 mL) at 0° C. is added a 2.5 M solution of n-butyl lithium in hexanes (5.8 mL, 14.7 mmol). The reaction is slowly warmed to room temperature over an hour, at which time it is re-cooled to −78° C. and methylchloroformate (0.74 mL, 9.6 mmol) is added. The reaction is brought to room temperature and permitted to stir for 16 hours. The reaction is then quenched with saturated aqueous NH4Cl and diluted with ethyl acetate. The layers are separated and the aqueous layer is extracted twice with ethyl acetate. The organic layers are combined, dried with Na2SO4, filtered, and concentrated. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 0:1 to 1:4) to provide 2,2-dimethyl-1,1-dioxo-1,2-dihydro-1lambda*6*-benzo[b]thiophen-3-one. 1H NMR (400 MHz, CDCl3) δ ppm 1.63 (s, 6 H), 7.79-7.86 (m, 1 H), 7.92-7.99 (m, 1 H), 8.03 (d, J=8.1 Hz, 2 H). is re-cooled to −78° C. is brought to room temperature The reaction is then quenched with saturated aqueous NH4Cl diluted with ethyl acetate The layers are separated the aqueous layer is extracted twice with ethyl acetate dried with Na2SO4 filtered concentrated The resulting residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 0:1 to 1:4)

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

Procedure: 3-Isopropylsulfonylaniline was synthesized in analogy to 3-ethylsulfonylaniline starting with 3-(isopropylsulfonyl)-benzene.