(5-bromo-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:

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

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

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: To a solution of 24.4 g (0.1214 mol) of 5-bromo-2-methylbenzylalcohol in 200 ml of dry diethyl ether was added dropwise 16.4 g (0.06067 mol) of phosphorous tribromide over 30 minutes with ice-cooling. After the mixture was stirred for 3 hours with ice-cooling, the reaction mixture was added to ice water (500 ml), and the mixture was separated. The organic layer was washed successively with water, a saturated aqueous solution of sodium bicarbonate and saturated brine, then dried and concentrated to obtain 29.07 g of 5-bromo-2-methylbenzylbromide as crystals. cooling cooling the mixture was separated The organic layer was washed successively with water a saturated aqueous solution of sodium bicarbonate and saturated brine, then dried concentrated

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

Procedure: To a suspension of 4.2 g (0.1094 mol) of lithium aluminum hydride in 250 ml of dry diethyl ether was added dropwise a solution of 33.4 g (0.1458 mol) of methyl 5-bromo-2-methylbenzoate in 50 ml of dry diethyl ether at room temperature over 30 minutes with ice-cooling under an atmosphere of nitrogen. The mixture was stirred at room temperature for 2 hours. About 10 ml of ethyl acetate was added dropwise thereto and further about 50 ml of tetrahydrofuran was added thereto. The mixture was added to 200 ml of a 10% aqueous solution of sulfuric acid and ice, and the mixture was separated. The organic layer was washed successively with water, a saturated aqueous solution of sodium bicarbonate and saturated brine, then dried and concentrated. The residue (28.7 g) was subjected to silica gel column chromatography (eluted with n-hexane:ethyl acetate=10:1 and then 5:1) to obtain 24.36 g of 5-bromo-2-methylbenzylalcohol as crystals. cooling under an atmosphere of nitrogen the mixture was separated The organic layer was washed successively with water a saturated aqueous solution of sodium bicarbonate and saturated brine, then dried concentrated eluted with n-hexane

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

Procedure: To a suspension of 4.2 g (0.1094 mol) of lithium aluminum hydride in 250 ml of dry diethyl ether was added dropwise a solution of 33.4 g (0.1458 mol) of methyl 5-bromo-2-methylbenzoate in 50 ml of dry diethyl ether at room temperature over 30 minutes with ice-cooling under an atmosphere of nitrogen. The mixture was stirred at room temperature for 2 hours. About 10 ml of ethyl acetate was added dropwise thereto and further about 50 ml of tetrahydrofuran was added thereto. The mixture was added to 200 ml of a 10% aqueous solution of sulfuric acid and ice, and the mixture was separated. The organic layer was washed successively with water, a saturated aqueous solution of sodium bicarbonate and saturated brine, then dried and concentrated. The residue (28.7 g) was subjected to silica gel column chromatography (eluted with n-hexane:ethyl acetate=10:1 and then 5:1) to obtain 24.36 g of 5-bromo-2-methylbenzylalcohol as crystals. cooling under an atmosphere of nitrogen the mixture was separated The organic layer was washed successively with water a saturated aqueous solution of sodium bicarbonate and saturated brine, then dried concentrated eluted with n-hexane

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

Procedure: 24.4 g (121 mmol) of 5-bromo-2-methylbenzyl alcohol was dissolved in 200 ml of anhydrous diethyl ether, and to the resulted solution was dropped 16.4 g (60.7 mmol) of phosphorus tribromide under ice cooling. The mixture was stirred further for 3 hours under ice cooling, then, the reaction solution was poured into ice water, then, separated. The organic layer was washed with water, saturated sodium bicarbonate solution and saline sequentially, dried over anhydrous magnesium sulfate, then, concentrated to obtain 29.1 g (110 mmol) of 5-bromo-2-methylbenzyl bromide in the form of brown solid. separated The organic layer was washed with water, saturated sodium bicarbonate solution and saline sequentially dried over anhydrous magnesium sulfate concentrated

Conditions: temp:17.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 161.2 g (810 mmol) of 5-bromo-2-methylbenzaldehyde was dissolved in 1.5 L of tetrahydrofuran and 150 ml of water, and to the resulted solution was dropped, at 15 to 20° C., a solution prepared by dissolving 10.0 g (264 mmol) of sodium boron hydride in 100 ml of a 0.1 wt % sodium hydroxide aqueous solution. After completion of dropping, the mixture was stirred at 15 to 20° C. for 4 hours. To the reaction solution was dropped 12.0 g of glacial acetic acid at 20° C. or lower, then, this was poured into ice water. The reaction solution was extracted with t-butyl methyl ether, the organic layer was washed with water, further washed twice with a saturated sodium bicarbonate solution, then, washed with saturated saline, and dried over anhydrous magnesium sulfate, then, concentrated to obtain 168 g of 5-bromo-2-methylbenzyl alcohol. a solution prepared The reaction solution was extracted with t-butyl methyl ether the organic layer was washed with water further washed twice with a saturated sodium bicarbonate solution washed with saturated saline dried over anhydrous magnesium sulfate concentrated