(4-Iodo-3-methyl-phenyl)-methanol

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

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

Procedure: To a solution of 4-iodo-3-methyl-benzoic acid (5.2 g, 20 mmol) in THF (30 mL), is added 2.0 M borane-dimethyl sulfide complex in THF (40.0 mL, 80 mmol) dropwise. The reaction mixture is stirred overnight. The reaction mixture is quenched carefully at 0° C. with methanol (20 mL) and the mixture is evaporated to dryness under reduced pressure. The residue is partitioned between EtOAc (80 mL) and water (60 mL). The organic phase is washed with brine (60 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to a residue. The residue is purified by flash chromatography (AnaLogix, gradient EtOAc/Hexane) to give (4-Iodo-3-methyl-phenyl)-methanol as white solid (4.7 g, 95%). 1HNMR (CDCl3) (ppm): 2.4 (3H, s), 4.55 (2H, s), 6.8-7.75 (3H, m). The reaction mixture is quenched carefully at 0° C. with methanol (20 mL) the mixture is evaporated to dryness under reduced pressure The residue is partitioned between EtOAc (80 mL) and water (60 mL) The organic phase is washed with brine (60 mL) dried (Na2SO4) filtered concentrated under reduced pressure to a residue The residue is purified by flash chromatography (AnaLogix, gradient EtOAc/Hexane)

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

Procedure: To a solution of 4-iodo-3-methyl-benzoic acid (5.2 g, 20 mmol) in THF (30 mL), is added 2.0 M borane-dimethyl sulfide complex in THF (40.0 mL, 80 mmol) dropwise. The reaction mixture is stirred overnight. The reaction mixture is quenched carefully at 0° C. with methanol (20 mL) and the mixture is evaporated to dryness under reduced pressure. The residue is partitioned between EtOAc (80 mL) and water (60 mL). The organic phase is washed with brine (60 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to a residue. The residue is purified by flash chromatography (AnaLogix, gradient EtOAc/Hexane) to give (4-Iodo-3-methyl-phenyl)-methanol as white solid (4.7 g, 95%). 1HNMR (CDCl3) (ppm): 2.4 (3H, s), 4.55 (2H, s), 6.8-7.75 (3H, m). The reaction mixture is quenched carefully at 0° C. with methanol (20 mL) the mixture is evaporated to dryness under reduced pressure The residue is partitioned between EtOAc (80 mL) and water (60 mL) The organic phase is washed with brine (60 mL) dried (Na2SO4) filtered concentrated under reduced pressure to a residue The residue is purified by flash chromatography (AnaLogix, gradient EtOAc/Hexane)

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

Procedure: To a solution of 4-iodo-3-methyl-benzoic acid (5.2 g, 20 mmol) in THF (30 mL), is added 2.0 M borane-dimethyl sulfide complex in THF (40.0 mL, 80 mmol) dropwise. The reaction mixture is stirred overnight. The reaction mixture is quenched carefully at 0° C. with methanol (20 mL) and the mixture is evaporated to dryness under reduced pressure. The residue is partitioned between EtOAc (80 mL) and water (60 mL). The organic phase is washed with brine (60 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to a residue. The residue is purified by flash chromatography (AnaLogix, gradient EtOAc/Hexane) to give (4-Iodo-3-methyl-phenyl)-methanol as white solid (4.7 g, 95%). 1HNMR (CDCl3) (ppm): 2.4 (3H, s), 4.55 (2H, s), 6.8-7.75 (3H, m). The reaction mixture is quenched carefully at 0° C. with methanol (20 mL) the mixture is evaporated to dryness under reduced pressure The residue is partitioned between EtOAc (80 mL) and water (60 mL) The organic phase is washed with brine (60 mL) dried (Na2SO4) filtered concentrated under reduced pressure to a residue The residue is purified by flash chromatography (AnaLogix, gradient EtOAc/Hexane)

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

Procedure: To a solution of 4-Iodo-3-methyl-benzoic acid (5.2 g, 20 mmol) in THF (30 mL) is added 2.0 M borane-dimethyl sulfide complex in THF (40.0 mL, 80 mmol) dropwise. The mixture is stirred overnight. The reaction mixture is quenched carefully at 0° C. with methanol (20 mL) and the mixture is evaporated to dryness under reduced pressure. The residue is partitioned between EtOAc (80 mL) and water (60 mL). The organic phase is washed with brine (60 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to a residue. The residue is purified by flash chromatography (gradient EtOAc/Hexane) to afford the title compound as white solid (4.7 g, 95%). 1HNMR (CDCl3) (ppm): 2.4 (3H, s), 4.55 (2H, s), 6.8-7.75 (3H, m). The reaction mixture is quenched carefully at 0° C. with methanol (20 mL) the mixture is evaporated to dryness under reduced pressure The residue is partitioned between EtOAc (80 mL) and water (60 mL) The organic phase is washed with brine (60 mL) dried (Na2SO4) filtered concentrated under reduced pressure to a residue The residue is purified by flash chromatography (gradient EtOAc/Hexane)

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

Procedure: To a solution of 4-iodo-3-methyl-benzoic acid (5.2 g, 20 mmol) in THF (30 mL), is added 2.0 M borane-dimethyl sulfide complex in THF (40.0 mL, 80 mmol) dropwise. The reaction mixture is stirred overnight. The reaction mixture is quenched carefully at 0° C. with methanol (20 mL) and the mixture is evaporated to dryness under reduced pressure. The residue is partitioned between EtOAc (80 mL) and water (60 mL). The organic phase is washed with brine (60 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to a residue. The residue is purified by flash chromatography (AnaLogix, gradient EtOAc/Hexane) to give (4-Iodo-3-methyl-phenyl)-methanol as white solid (4.7 g, 95%). 1HNMR (CDCl3) (ppm): 2.4 (3H, s), 4.55 (2H, s), 6.8-7.75 (3H, m). The reaction mixture is quenched carefully at 0° C. with methanol (20 mL) the mixture is evaporated to dryness under reduced pressure The residue is partitioned between EtOAc (80 mL) and water (60 mL) The organic phase is washed with brine (60 mL) dried (Na2SO4) filtered concentrated under reduced pressure to a residue The residue is purified by flash chromatography (AnaLogix, gradient EtOAc/Hexane)