2-(3-bromophenyl)propan-2-ol

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

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

Procedure: In a nitrogen atmosphere with cooling with ice, 5.29 mL of 3′-bromoacetophenone was added to 25 mL of 2 M methylmagnesium iodide/diethyl ether solution and 100 mL of diethyl ether, and stirred for 20 minutes. Water and 2 N hydrochloric acid were added to the reaction liquid, extracted with ethyl acetate, washed with aqueous saturated sodium hydrogencarbonate solution and saturated saline water, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure to obtain crude 2-(3-bromophenyl)propan-2-ol. extracted with ethyl acetate washed with aqueous saturated sodium hydrogencarbonate solution and saturated saline water dried with anhydrous magnesium sulfate The solvent was evaporated away under reduced pressure

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

Procedure: In a nitrogen atmosphere with cooling with ice, 5.29 mL of 3′-bromoacetophenone was added to 25 mL of 2 M methylmagnesium iodide/diethyl ether solution and 100 mL of diethyl ether, and stirred for 20 minutes. Water and 2 N hydrochloric acid were added to the reaction liquid, extracted with ethyl acetate, washed with aqueous saturated sodium hydrogencarbonate solution and saturated saline water, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure to obtain crude 2-(3-bromophenyl)propan-2-ol. extracted with ethyl acetate washed with aqueous saturated sodium hydrogencarbonate solution and saturated saline water dried with anhydrous magnesium sulfate The solvent was evaporated away under reduced pressure

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

Procedure: To a stirred solution of methylmagnesium-bromide (60 mL of a 3.0 M solution in diethyl ether) at 0° C. was added dropwise a solution of 3-bromoacetophenone (29.8 grams) in 75 mL of diethyl ether. Once the addition was complete, the mixture was stirred for 0.5 hours and poured into water. The aqueous phase was acidified with 1M hydrochloric acid and extracted with three portions of diethyl ether. The combined ether layers were washed with saturated sodium bicarbonate, concentrated to afford 30.4 grams of the title compound. 1H NMR δ 7.72 (br s, 1), 7.49 (d, 1, J=7.8), 7.37 (d, 1, J=7.9), 7.25 (dd, 1, J=7.8, 7.9), 4.19 (s, 1), 1.50 (brs, 6). Once the addition extracted with three portions of diethyl ether The combined ether layers were washed with saturated sodium bicarbonate concentrated

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

Procedure: To a solution of 3.34 g (16.8 mmol) of 3'-bromoacetophenone in dry diethyl ether (68 ml) was added 1.4M diethyl ether solution of methyllithium (18.0 ml, 25.2 mmol) in an atmosphere of argon at 0° C., and the mixture was allowed to react for 30 min. To the solution was added a saturated aqueous solution of ammonium chloride, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography for separation and purification. Elution with dichloromethane-methanol yielded 3.47 g (16.1 mmol) of 3-(α-hydroxyisopropyl)-1-bromobenzene. to react for 30 min the mixture was extracted with ethyl acetate The organic layer was washed with water concentrated under reduced pressure The residue thus obtained was subjected to silica gel column chromatography for separation and purification Elution with dichloromethane-methanol

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

Procedure: To a solution of 3.34 g (16.8 mmol) of 3'-bromoacetophenone in dry diethyl ether (68 ml) was added 1.4M diethyl ether solution of methyllithium (18.0 ml, 25.2 mmol) in an atmosphere of argon at 0° C., and the mixture was allowed to react for 30 min. To the solution was added a saturated aqueous solution of ammonium chloride, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography for separation and purification. Elution with dichloromethane-methanol yielded 3.47 g (16.1 mmol) of 3-(α-hydroxyisopropyl)-1-bromobenzene. to react for 30 min the mixture was extracted with ethyl acetate The organic layer was washed with water concentrated under reduced pressure The residue thus obtained was subjected to silica gel column chromatography for separation and purification Elution with dichloromethane-methanol

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

Procedure: Under an argon stream, 6.5 g of 3-bromoacetophenone are placed in a round-bottomed flask and dissolved in 544 ml of diethyl ether and 272 ml of tetrahydrofuran. The mixture is cooled to 0° C. using an ice bath, and 100 ml of a 1M solution of methylmagnesium bromide in dibutyl ether are added thereto, dropwise. The mixture is stirred at 0° C. for 1 h and 400 ml of a saturated aqueous solution of ammonium chloride are added. The organic phase is separated, dried over magnesium sulphate and concentrated under reduced pressure. 10.0 g of compound are obtained. 1H NMR (DMSO-d6, δ in ppm): 1.45 (s, 6H); 5.15 (s, 1H); 7.25 (t, 1H); 7.4 (d, 1H); 7.45 (d, 1H); 7.65 (s, 1H). The organic phase is separated dried over magnesium sulphate concentrated under reduced pressure

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

Procedure: To 75 mmol of methylmagnesium bromide in 25 mL of ether stirring at 6° C. is added, dropwise over 10 min, a solution of methyl-3-bromobenzoate (4.3 g, 20 mmol) in 25 mL of dry THF. The mixture is then allowed to warm to ambient temperature and stirred for 3.5 h, then cooled to 0° C. and quenched by dropwise addition of aqueous 10% HCl. The acidified mixture is extracted twice with ethyl acetate, and the combined organic phases are washed with 1 N NaHCO3 and with brine. The solution is dried over Na2SO4, concentrated, and chromatographed over silica gel, eluting with 15% ethyl acetate in heptane, to afford 4.00 g (18.6 mmol, 93%) of 2-(3-bromophenyl)-2-propanol 27 as a pale yellow oil: 1H NMR (CDCl3) δ 7.65 (t, J=2 Hz, 1H), 7.39 (m, 2H), 7.20 (t, J=8 Hz, 1H), 1.78 (br s, 1H), 1.57 (s, 6H). cooled to 0° C. quenched by dropwise addition of aqueous 10% HCl The acidified mixture is extracted twice with ethyl acetate the combined organic phases are washed with 1 N NaHCO3 and with brine The solution is dried over Na2SO4 concentrated chromatographed over silica gel eluting with 15% ethyl acetate in heptane

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

Procedure: To 75 mmol of methylmagnesium bromide in 25 mL of ether stirring at 6° C. is added, dropwise over 10 min, a solution of methyl-3-bromobenzoate (4.3 g, 20 mmol) in 25 mL of dry THF. The mixture is then allowed to warm to ambient temperature and stirred for 3.5 h, then cooled to 0° C. and quenched by dropwise addition of aqueous 10% HCl. The acidified mixture is extracted twice with ethyl acetate, and the combined organic phases are washed with 1 N NaHCO3 and with brine. The solution is dried over Na2SO4, concentrated, and chromatographed over silica gel, eluting with 15% ethyl acetate in heptane, to afford 4.00 g (18.6 mmol, 93%) of 2-(3-bromophenyl)-2-propanol 27 as a pale yellow oil: 1H NMR (CDCl3) δ 7.65 (t, J=2 Hz, 1 H), 7.39 (m, 2 H), 7.20 (t, J=8 Hz, 1 H), 1.78 (br s, 1 H), 1.57 (s, 6 H). cooled to 0° C. quenched by dropwise addition of aqueous 10% HCl The acidified mixture is extracted twice with ethyl acetate the combined organic phases are washed with 1 N NaHCO3 and with brine The solution is dried over Na2SO4 concentrated chromatographed over silica gel eluting with 15% ethyl acetate in heptane

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

Procedure: Under a stream of argon, 6.5 g of 3-bromoacetophenone are placed in a round-bottomed flask and dissolved in 544 ml of diethyl ether and 272 ml of tetrahydrofuran. The mixture is cooled at 0° C. using an ice bath, and 100 ml of a 1M solution of methylmagnesium bromide in dibutyl ether are added thereto, dropwise. The mixture is stirred at 0° C. for 1 h and 400 ml of a saturated aqueous solution of ammonium chloride are added. The organic phase is separated, dried over magnesium sulphate and concentrated under reduced pressure. 10.0 g of compound are obtained. The organic phase is separated dried over magnesium sulphate concentrated under reduced pressure

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

Procedure: To a mixture of the 2-(3-bromo-phenyl)-propan-2-ol and (0.76 g, 3.6 mmol) and chloro-acetonitrile (7 mL) was added acetic acid (0.6 mL) and the resulting mixture was cooled to 0° C. Concentrated sulfuric acid (0.6 mL) was added dropwise and the mixture was brought to room temperature and stirred for 17 h. Mixture was poured into ice-water (10 mL) and extracted with ethylacetate. The extracts were combined, dried over magnesium sulfate and concentrated to afford a white solid. M+1=291. was brought to room temperature extracted with ethylacetate dried over magnesium sulfate concentrated to afford a white solid

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

Procedure: In a nitrogen atmosphere with cooling with ice, 5.29 mL of 3′-bromoacetophenone was added to 25 mL of 2 M methylmagnesium iodide/diethyl ether solution and 100 mL of diethyl ether, and stirred for 20 minutes. Water and 2 N hydrochloric acid were added to the reaction liquid, extracted with ethyl acetate, washed with aqueous saturated sodium hydrogencarbonate solution and saturated saline water, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure to obtain crude 2-(3-bromophenyl)propan-2-ol. extracted with ethyl acetate washed with aqueous saturated sodium hydrogencarbonate solution and saturated saline water dried with anhydrous magnesium sulfate The solvent was evaporated away under reduced pressure