3-methylnaphthalen-2-ol

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-chlorosuccinimide (8.02 g, 60.05 mmol) in dichloromethane (475 mL) at −78° C. was added zirconium(IV) chloride (2.80 g, 12.01 mmol), followed by 3-methyl-naphthalen-2-ol (CombiBlocks, 9.5 g, 60.05 mmol) under argon. The reaction mixture was stirred at −78° C. for 5 minutes, the cooling bath was removed and the reaction was stirred at room temperature for 5 h. The reaction was quenched with saturated sodium bicarbonate solution and stirred for 5 minutes. The mixture was diluted with H2O, extracted with dichloromethane (3×) and the combined organic layer was dried (MgSO4), filtered, concentrated and purified by flash column chromatography (silica gel, 0 to 10% ethyl acetate/hexanes) to give 1-chloro-3-methyl-naphthalen-2-ol. the cooling bath was removed the reaction was stirred at room temperature for 5 h The reaction was quenched with saturated sodium bicarbonate solution stirred for 5 minutes The mixture was diluted with H2O extracted with dichloromethane (3×) the combined organic layer was dried (MgSO4) filtered concentrated purified by flash column chromatography (silica gel, 0 to 10% ethyl acetate/hexanes)

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-chlorosuccinimide (8.02 g, 60.05 mmol) in dichloromethane (475 mL) at −78° C. was added zirconium(IV) chloride (2.80 g, 12.01 mmol), followed by 3-methyl-naphthalen-2-ol (CombiBlocks, 9.5 g, 60.05 mmol) under argon. The reaction mixture was stirred at −78° C. for 5 minutes, the cooling bath was removed and the reaction was stirred at room temperature for 5 h. The reaction was quenched with saturated sodium bicarbonate solution and stirred for 5 minutes. The mixture was diluted with H2O, extracted with dichloromethane (3×) and the combined organic layer was dried (MgSO4), filtered, concentrated and purified by flash column chromatography (silica gel, 0 to 10% ethyl acetate/hexanes) to give 1-chloro-3-methyl-naphthalen-2-ol. the cooling bath was removed the reaction was stirred at room temperature for 5 h The reaction was quenched with saturated sodium bicarbonate solution stirred for 5 minutes The mixture was diluted with H2O extracted with dichloromethane (3×) the combined organic layer was dried (MgSO4) filtered concentrated purified by flash column chromatography (silica gel, 0 to 10% ethyl acetate/hexanes)

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-chlorosuccinimide (8.02 g, 60.05 mmol) in dichloromethane (475 mL) at −78° C. was added zirconium(IV) chloride (2.80 g, 12.01 mmol), followed by 3-methyl-naphthalen-2-ol (CombiBlocks, 9.5 g, 60.05 mmol) under argon. The reaction mixture was stirred at −78° C. for 5 minutes, the cooling bath was removed and the reaction was stirred at room temperature for 5 h. The reaction was quenched with saturated sodium bicarbonate solution and stirred for 5 minutes. The mixture was diluted with H2O, extracted with dichloromethane (3×) and the combined organic layer was dried (MgSO4), filtered, concentrated and purified by flash column chromatography (silica gel, 0 to 10% ethyl acetate/hexanes) to give 1-chloro-3-methyl-naphthalen-2-ol. 1H NMR (400 MHz, CDCl3) δ 8.01 (d, J=8.2 Hz, 1H), 7.72 (d, J=8.2 Hz, 1H), 7.54 (s, 1H), 7.52 (dd, J=8.2, 8.2 Hz, 1H), 7.36 (dd, J=8.2, 8.2 Hz, 1H), 5.99 (s, 1H), 2.47 (s, 3H). the cooling bath was removed the reaction was stirred at room temperature for 5 h The reaction was quenched with saturated sodium bicarbonate solution stirred for 5 minutes The mixture was diluted with H2O extracted with dichloromethane (3×) the combined organic layer was dried (MgSO4) filtered concentrated purified by flash column chromatography (silica gel, 0 to 10% ethyl acetate/hexanes)

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

Procedure: 3-Methylnaphthalen-2-ol (4A) (2.09 g, 13.2 mmol) was taken in acetic acid (50 mL) and bromine (2.11 g) was added to it. The mixture was stirred at room temperature for 20 minutes, concentrated and purified by flash chromatography (silica gel, ethyl acetate/hexanes) to give the desired product (2.7 g, 80%). 1H-NMR: 300 MHz, (CDCl3) δ 7.98 (d, 1 H), 7.60 (d, 1 H), 7.58 (s, 1 H), 7.53 (dd, 1 H), 7.38 (dd, 1 H), 6.05 (s, 1 H), 2.48 (s, 3 H). concentrated purified by flash chromatography (silica gel, ethyl acetate/hexanes)

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-chlorosuccinimide (8.02 g, 60.05 mmol) in dichloromethane (475 mL) at −78° C. was added zirconium(IV)chloride (2.80 g, 12.01 mmol), followed by 3-methyl-naphthalen-2-ol (4A) (9.5 g, 60.05 mmol) under Ar. The reaction mixture was stirred at −78° C. for minutes, the cooling bath was removed and the reaction was stirred at room temperature for 5 h. The reaction was quenched with saturated sodium bicarbonate solution and stirred for 5 minutes. The mixture was diluted with H2O, extracted with dichloromethane (3×) and the combined organic layer was dried (MgSO4), filtered, concentrated and purified by flash column chromatography (silica gel, 0 to 10% ethyl acetate/hexanes) to give 4B as a white solid (9.05 g, 78%). the cooling bath was removed the reaction was stirred at room temperature for 5 h The reaction was quenched with saturated sodium bicarbonate solution stirred for 5 minutes The mixture was diluted with H2O extracted with dichloromethane (3×) the combined organic layer was dried (MgSO4) filtered concentrated purified by flash column chromatography (silica gel, 0 to 10% ethyl acetate/hexanes)

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-chlorosuccinimide (8.02 g, 60.05 mmol) in dichloromethane (475 mL) at −78° C. was added zirconium(IV) chloride (2.80 g, 12.01 mmol), followed by 3-methyl-naphthalen-2-ol (CombiBlocks, 9.5 g, 60.05 mmol) under argon. The reaction mixture was stirred at −78° C. for 5 minutes, the cooling bath was removed and the reaction was stirred at room temperature for 5 h. The reaction was quenched with saturated sodium bicarbonate solution and stirred for 5 minutes. The mixture was diluted with H2O, extracted with dichloromethane (3×) and the combined organic layer was dried (MgSO4), filtered, concentrated and purified by flash column chromatography (silica gel, 0 to 10% ethyl acetate/hexanes) to give 1-chloro-3-methyl-naphthalen-2-ol. the cooling bath was removed the reaction was stirred at room temperature for 5 h The reaction was quenched with saturated sodium bicarbonate solution stirred for 5 minutes The mixture was diluted with H2O extracted with dichloromethane (3×) the combined organic layer was dried (MgSO4) filtered concentrated purified by flash column chromatography (silica gel, 0 to 10% ethyl acetate/hexanes)

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-chlorosuccinimide (8.02 g, 60.05 mmol) in dichloromethane (475 mL) at −78° C. was added zirconium(IV) chloride (2.80 g, 12.01 mmol), followed by 3-methyl-naphthalen-2-ol (CombiBlocks, 9.5 g, 60.05 mmol) under argon. The reaction mixture was stirred at −78° C. for 5 minutes, the cooling bath was removed and the reaction was stirred at room temperature for 5 h. The reaction was quenched with saturated sodium bicarbonate solution and stirred for 5 minutes. The mixture was diluted with H2O, extracted with dichloromethane (3×) and the combined organic layer was dried (MgSO4), filtered, concentrated and purified by flash column chromatography (silica gel, 0 to 10% ethyl acetate/hexanes) to give 1-chloro-3-methyl-naphthalen-2-ol. 1H NMR (400 MHz, CDCl3) δ 8.01 (d, J=8.2 Hz, 1H), 7.72 (d, J=8.2 Hz, 1H), 7.54 (s, 1H), 7.52 (dd, J=8.2, 8.2 Hz, 1H), 7.36 (dd, J=8.2, 8.2 Hz, 1H), 5.99 (s, 1H), 2.47 (s, 3H). the cooling bath was removed the reaction was stirred at room temperature for 5 h The reaction was quenched with saturated sodium bicarbonate solution stirred for 5 minutes The mixture was diluted with H2O extracted with dichloromethane (3×) the combined organic layer was dried (MgSO4) filtered concentrated purified by flash column chromatography (silica gel, 0 to 10% ethyl acetate/hexanes)

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

Procedure: 3-Methylnaphthalen-2-ol (4A) (2.09 g, 13.2 mmol) was taken in acetic acid (50 mL) and bromine (2.11 g) was added to it. The mixture was stirred at room temperature for 20 minutes, concentrated and purified by flash chromatography (silica gel, ethyl acetate/hexanes) to give the desired product (2.7 g, 80%). 1H-NMR: 300 MHz, (CDCl3) δ 7.98 (d, 1 H), 7.60 (d, 1 H), 7.58 (s, 1 H), 7.53 (dd, 1 H), 7.38 (dd, 1 H), 6.05 (s, 1 H), 2.48 (s, 3 H). concentrated purified by flash chromatography (silica gel, ethyl acetate/hexanes)

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-chlorosuccinimide (8.02 g, 60.05 mmol) in dichloromethane (475 mL) at −78° C. was added zirconium(IV)chloride (2.80 g, 12.01 mmol), followed by 3-methyl-naphthalen-2-ol (4A) (9.5 g, 60.05 mmol) under Ar. The reaction mixture was stirred at −78° C. for minutes, the cooling bath was removed and the reaction was stirred at room temperature for 5 h. The reaction was quenched with saturated sodium bicarbonate solution and stirred for 5 minutes. The mixture was diluted with H2O, extracted with dichloromethane (3×) and the combined organic layer was dried (MgSO4), filtered, concentrated and purified by flash column chromatography (silica gel, 0 to 10% ethyl acetate/hexanes) to give 4B as a white solid (9.05 g, 78%). the cooling bath was removed the reaction was stirred at room temperature for 5 h The reaction was quenched with saturated sodium bicarbonate solution stirred for 5 minutes The mixture was diluted with H2O extracted with dichloromethane (3×) the combined organic layer was dried (MgSO4) filtered concentrated purified by flash column chromatography (silica gel, 0 to 10% ethyl acetate/hexanes)