2-(4-bromo-2-chlorophenyl)propan-2-ol

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

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

Procedure: A solution of 370 mg (1.48 mmol) of 2-(4-bromo-2-chloro-phenyl)-propan-2-ol in 2 ml DMF was added to a suspension of sodium hydride (65 mg, ˜60% dispersion in oil) in 2 ml DMF at 0° C. The mixture was stirred at 0° C. for 30 min and then 111 μl (1.78 mmol) of methyl iodide were added. The reaction mixture was then warmed to rt and stirring was continued overnight. Then water was added and the mixture was extracted with ether. The organic phase was washed with water and brine, dried (MgSO4), filtered, and concentrated in vacuo to give a residue which was purified by flash column chromatography (1:9 ether/pentane). The title compound was obtained as a colorless liquid (310 mg, 79%). 1H NMR (CDCl3, 300 MHz): δ 1.64 (s, 6H), 3.13 (s, 3H), 7.35 (m, 2H), 7.54 (d, J=1.7 Hz, 1H). The reaction mixture was then warmed to rt stirring was continued overnight the mixture was extracted with ether The organic phase was washed with water and brine dried (MgSO4) filtered concentrated in vacuo to give a residue which was purified by flash column chromatography (1:9 ether/pentane)

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

Procedure: A solution of 370 mg (1.48 mmol) of 2-(4-bromo-2-chloro-phenyl)-propan-2-ol in 2 ml DMF was added to a suspension of sodium hydride (65 mg, ˜60% dispersion in oil) in 2 ml DMF at 0° C. The mixture was stirred at 0° C. for 30 min and then 111 μl (1.78 mmol) of methyl iodide were added. The reaction mixture was then warmed to rt and stirring was continued overnight. Then water was added and the mixture was extracted with ether. The organic phase was washed with water and brine, dried (MgSO4), filtered, and concentrated in vacuo to give a residue which was purified by flash column chromatography (1:9 ether/pentane). The title compound was obtained as a colorless liquid (310 mg, 79%). 1H NMR (CDCl3, 300 MHz): δ 1.64 (s, 6H), 3.13 (s, 3H), 7.35 (m, 2H), 7.54 (d, J=1.7 Hz, 1H). The reaction mixture was then warmed to rt stirring was continued overnight the mixture was extracted with ether The organic phase was washed with water and brine dried (MgSO4) filtered concentrated in vacuo to give a residue which was purified by flash column chromatography (1:9 ether/pentane)

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

Procedure: 1.88 ml of a 3 molar solution of methyl magnesium bromide in ether were added dropwise to a solution of 470 mg (1.88 mmol) of 4-bromo-2-chloro-benzoic acid methyl ester [CAS 185312-82-7] in 20 ml THF at −78° C. The reaction mixture was then warmed to rt and stirred overnight. The mixture was then poured into sat. ammonium chloride solution and extracted with ether. The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated in vacuo to give a residue which was purified by flash column chromatography (0 to 20% ether in pentane). The title compound was obtained as a colorless liquid (415 mg, 82%). 1H NMR (CDCl3, 300 MHz): δ 1.71 (s, 6H), 2.39 (s, 1H), 7.38 (dd, J=8.5 and 2.1 Hz, 1H), 7.52 (d, J=2.1 Hz, 1H), 7.58 (d, J=8.5 Hz, 1H). extracted with ether The combined organic layers were washed with brine dried (MgSO4) filtered concentrated in vacuo to give a residue which was purified by flash column chromatography (0 to 20% ether in pentane)

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

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

Procedure: Triethylsilane (1.8 mL) and trifluoroacetic acid (5.8 mL) were added to a solution of 2-(4-bromo-2-chlorophenyl)propan-2-ol (1.9 g) in dichloromethane (76 mL), and the mixture was stirred at room temperature for one day. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane only) to give the title compound as a colorless oil (1.74 g, 98%). followed by extraction with ethyl acetate The organic layer was dried over anhydrous magnesium sulfate filtered The solvent was then evaporated under reduced pressure The residue was purified by silica gel column chromatography (hexane only)

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

Procedure: A solution of 370 mg (1.48 mmol) of 2-(4-bromo-2-chloro-phenyl)-propan-2-ol in 2 ml DMF was added to a suspension of sodium hydride (65 mg, ˜60% dispersion in oil) in 2 ml DMF at 0° C. The mixture was stirred at 0° C. for 30 min and then 111 μl (1.78 mmol) of methyl iodide were added. The reaction mixture was then warmed to rt and stirring was continued overnight. Then water was added and the mixture was extracted with ether. The organic phase was washed with water and brine, dried (MgSO4), filtered, and concentrated in vacuo to give a residue which was purified by flash column chromatography (1:9 ether/pentane). The title compound was obtained as a colorless liquid (310 mg, 79%). 1H NMR (CDCl3, 300 MHz): δ 1.64 (s, 6H), 3.13 (s, 3H), 7.35 (m, 2H), 7.54 (d, J=1.7 Hz, 1H). The reaction mixture was then warmed to rt stirring was continued overnight the mixture was extracted with ether The organic phase was washed with water and brine dried (MgSO4) filtered concentrated in vacuo to give a residue which was purified by flash column chromatography (1:9 ether/pentane)

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

Procedure: 1.88 ml of a 3 molar solution of methyl magnesium bromide in ether were added dropwise to a solution of 470 mg (1.88 mmol) of 4-bromo-2-chloro-benzoic acid methyl ester [CAS 185312-82-7] in 20 ml THF at −78° C. The reaction mixture was then warmed to rt and stirred overnight. The mixture was then poured into sat. ammonium chloride solution and extracted with ether. The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated in vacuo to give a residue which was purified by flash column chromatography (0 to 20% ether in pentane). The title compound was obtained as a colorless liquid (415 mg, 82%). 1H NMR (CDCl3, 300 MHz): δ 1.71 (s, 6H), 2.39 (s, 1H), 7.38 (dd, J=8.5 and 2.1 Hz, 1H), 7.52 (d, J=2.1 Hz, 1H), 7.58 (d, J=8.5 Hz, 1H). extracted with ether The combined organic layers were washed with brine dried (MgSO4) filtered concentrated in vacuo to give a residue which was purified by flash column chromatography (0 to 20% ether in pentane)

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