[5-bromo-2-(methoxymethoxy)phenyl]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: To a solution of 5-bromo-2-methoxymethoxybenzyl alcohol (27.2 g) and triethylamine (23 ml) in dichloromethane (550 ml) was added, at 0° C., methanesulfonyl chloride (13.9 g). The mixture was stirred for 15 hours, while warming up to room temperature. The reaction mixture was poured into water, which was subjected to extraction with ethyl acetate. The extract solution was washed with an aqueous saline solution, which was then dried (anhydrous magnesium sulfate), followed by concentration to give an oily product. The oily product was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane) to give 5-bromo-2-methoxymethoxybenzyl chloride (21.6 g) as an oily product. was subjected to extraction with ethyl acetate The extract solution was washed with an aqueous saline solution, which was then dried (anhydrous magnesium sulfate) followed by concentration to give an oily product The oily product was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane)

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

Procedure: To a solution of 5-bromo-2-methoxymethoxybenzyl alcohol (27.2 g) and triethylamine (23 ml) in dichloromethane (550 ml) was added, at 0° C., methanesulfonyl chloride (13.9 g). The mixture was stirred for 15 hours, while warming up to room temperature. The reaction mixture was poured into water, which was subjected to extraction with ethyl acetate. The extract solution was washed with an aqueous saline solution, which was then dried (anhydrous magnesium sulfate), followed by concentration to give an oily product. The oily product was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane) to give 5-bromo-2-methoxymethoxybenzyl chloride (21.6 g) as an oily product. was subjected to extraction with ethyl acetate The extract solution was washed with an aqueous saline solution, which was then dried (anhydrous magnesium sulfate) followed by concentration to give an oily product The oily product was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane)

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

Procedure: To a solution of 5-bromo-2-methoxymethoxybenzaldehyde (5.00 g) in methanol (50 ml) was added, at 0° C., sodium borohydride (0.46 g). The mixture was stirred for 30 minutes at the same temperature, which was then concentrated. To the concentrate was added ethyl acetate, and the mixture was washed with an aqueous solution of potassium hydrogensulfate and a saturated aqueous saline solution, successively. The organic layer was dried (anhydrous magnesium sulfate), which was then concentrated to leave 5-bromo-2-methoxymethoxybenzyl alcohol (5.04 g) as a pale yellow oily product. was then concentrated To the concentrate was added ethyl acetate the mixture was washed with an aqueous solution of potassium hydrogensulfate The organic layer was dried (anhydrous magnesium sulfate), which was then concentrated

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 5-bromo-2-methoxymethoxybenzyl alcohol (27.2 g) and triethylamine (23 ml) in dichloromethane (550 ml) was added, at 0° C., methanesulfonyl chloride (13.9 g). The mixture was stirred for 15 hours, while warming up to room temperature. The reaction mixture was poured into water, which was subjected to extraction with ethyl acetate. The extract solution was washed with an aqueous saline solution, which was then dried (anhydrous magnesium sulfate), followed by concentration to give an oily product. The oily product was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane) to give 5-bromo-2-methoxymethoxybenzyl chloride (21.6 g) as an oily product. was subjected to extraction with ethyl acetate The extract solution was washed with an aqueous saline solution, which was then dried (anhydrous magnesium sulfate) followed by concentration to give an oily product The oily product was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane)

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

Procedure: To a solution of 5-bromo-2-methoxymethoxybenzaldehyde (5.00 g) in methanol (50 ml) was added, at 0° C., sodium borohydride (0.46 g). The mixture was stirred for 30 minutes at the same temperature, which was then concentrated. To the concentrate was added ethyl acetate, and the mixture was washed with an aqueous solution of potassium hydrogensulfate and a saturated aqueous saline solution, successively. The organic layer was dried (anhydrous magnesium sulfate), which was then concentrated to leave 5-bromo-2-methoxymethoxybenzyl alcohol (5.04 g) as a pale yellow oily product. was then concentrated To the concentrate was added ethyl acetate the mixture was washed with an aqueous solution of potassium hydrogensulfate The organic layer was dried (anhydrous magnesium sulfate), which was then concentrated

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