(3-chloro-2-methylphenyl)methanol

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

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

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

Procedure: LAH (61.00 mL, 1.0 M in THF, 61.00 mmol) was added to a solution of 3-chloro-2-methyl-benzoic acid methyl ester (4.50 g, 24.40 mmol) in THF at 0° C. The reaction mixture was stirred for 1 hour, water was added to quench the reaction. The aqueous layer was extracted with Et2O (3×150 mL), and the combined organic phases were washed with brine (1×150 mL) and dried over MgSO4. Purification by column chromatography using hex:EtOAc (4:1) as the eluant afforded 3.97 g of the title compound. Spectroscopic data: 1H NMR (300 MHz, CDCl3.) δ 1.94 (br s, 1H), 2.36 (s, 3H), 4.67 (br s, 2H), 7.11 (t, J=7.765 Hz, 1H), 7.245 (d, J=7.03 Hz, 1H), 7.30 (d, J=7.91 Hz, 1H). to quench the reaction The aqueous layer was extracted with Et2O (3×150 mL) the combined organic phases were washed with brine (1×150 mL) dried over MgSO4 Purification by column chromatography

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

Procedure: 910 mg of 3-chloro-2-methylbenzylalcohol was dissolved in 10 mL of methylene chloride, 1.21 mL of triethylamine and 495 μL of methanesulfonyl chloride were added thereto at room temperature, followed by stirring for 3 hours. After completion of the reaction, a saturated aqueous sodium hydrogen carbonate solution was added to the reaction liquid, followed by extraction with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 700 mg (yield 69%) of a title compound as a white solid. at room temperature After completion of the reaction followed by extraction with chloroform The organic layer was washed with saturated brine dried over anhydrous sodium sulfate concentrated under reduced pressure

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

Procedure: 910 mg of 3-chloro-2-methylbenzylalcohol was dissolved in 10 mL of methylene chloride, 1.21 mL of triethylamine and 495 μL of methanesulfonyl chloride were added thereto at room temperature, followed by stirring for 3 hours. After completion of the reaction, a saturated aqueous sodium hydrogen carbonate solution was added to the reaction liquid, followed by extraction with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 700 mg (yield 69%) of a title compound as a white solid. at room temperature After completion of the reaction followed by extraction with chloroform The organic layer was washed with saturated brine dried over anhydrous sodium sulfate concentrated under reduced pressure

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

Procedure: 910 mg of 3-chloro-2-methylbenzylalcohol was dissolved in 10 mL of methylene chloride, 1.21 mL of triethylamine and 495 μL of methanesulfonyl chloride were added thereto at room temperature, followed by stirring for 3 hours. After completion of the reaction, a saturated aqueous sodium hydrogen carbonate solution was added to the reaction liquid, followed by extraction with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 700 mg (yield 69%) of a title compound as a white solid. at room temperature After completion of the reaction followed by extraction with chloroform The organic layer was washed with saturated brine dried over anhydrous sodium sulfate concentrated under reduced pressure

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

Procedure: To a solution of 1.70 g of 3-chloro-2-methylbenzoic acid in 20 mL of THF was added dropwise 20 mL of a borane/THF complex under ice-cooling, followed by stirring at room temperature for 2 hours. After completion of the reaction, 1 N hydrochloric acid was added to the reaction liquid, followed by extraction with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 1.52 g (yield 97%) of a title compound as a white crystal. cooling was added to the reaction liquid followed by extraction with chloroform The organic layer was washed with saturated brine dried over anhydrous sodium sulfate concentrated under reduced pressure

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

Procedure: To a solution of phosphorus tribromide (0.422 mL, 4.47 mmol) in Toluene (30 mL) was added (3-chloro-2-methylphenyl)methanol (2 g, 12.77 mmol). The reaction was stirred at RT overnight. The solvent was removed and the residue was partitioned between EtOAc and brine. The organic layer was concentrated and the residue was purified by biotage (5% EA/hexane) to give the product (2.0 g, 71%). 1H NMR (400 MHz, CDCl3) δppm 7.36 (m, 1H), 7.24 (m, 1H), 7.12 (m, 1H), 4.56 (s, 2H). 2.48 (s, 3H). The solvent was removed the residue was partitioned between EtOAc and brine The organic layer was concentrated the residue was purified by biotage (5% EA/hexane)

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

Procedure: A solution of lithium aluminium hydride (29.8 mL, 29.8 mmol) in THF was cooled to 0° C., and a solution of methyl 3-chloro-2-methylbenzoate (2.5 g, 13.54 mmol) in Tetrahydrofuran (THF) (20 mL) was added dropwise. The mixture was stirred at 0° C. for half hour, warmed up to RT gradually, and stirred at RT for 2 hours. Water and 6N NaOH (4 ml) were added to quench the reaction. The mixture was filtered and the filtrate was concentrated to afford the crude product as a white solid (2.0 g, 94%). 1H NMR (400 MHz, CDCl3) δppm 7.30˜7.35 (m, 2H), 7.16 (m, 1H), 4.74 (s, 2H), 2.40 (s, 3H). warmed up to RT gradually stirred at RT for 2 hours to quench the reaction The mixture was filtered the filtrate was concentrated

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

Procedure: LAH (61.00 mL, 1.0 M in THF, 61.00 mmol) was added to a solution of 3-chloro-2-methyl-benzoic acid methyl ester (4.50 g, 24.40 mmol) in THF at 0° C. The reaction mixture was stirred for 1 hour, water was added to quench the reaction. The aqueous layer was extracted with Et2O (3×150 mL), and the combined organic phases were washed with brine (1×150 mL) and dried over MgSO4. Purification by column chromatography using hex:EtOAc (4:1) as the eluant afforded 3.97 g of the title compound. Spectroscopic data: 1H NMR (300 MHz, CDCl3.) δ 1.94 (br s, 1H), 2.36 (s, 3H), 4.67 (br s, 2H), 7.11 (t, J=7.765 Hz, 1H), 7.245 (d, J=7.03 Hz, 1H), 7.30 (d, J=7.91 Hz, 1H). to quench the reaction The aqueous layer was extracted with Et2O (3×150 mL) the combined organic phases were washed with brine (1×150 mL) dried over MgSO4 Purification by column chromatography