(5-bromo-2-chlorophenyl)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: Imidazole (5.22 g) and tert-butyldimethylsilyl chloride (8.64 g) were added to a solution of (5-bromo-2-chlorophenyl)methanol (8.47 g) in DMF (80 ml). The reaction mixture was stirred at room temperature overnight. The mixture was diluted with ethyl acetate and washed twice with water. The aqueous layer was again extracted with ethyl acetate. The combined organic layer was washed with brine and dried over anhydrous magnesium sulfate. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound (12.6 g). washed twice with water The aqueous layer was again extracted with ethyl acetate The combined organic layer was washed with brine dried over anhydrous magnesium sulfate The filtrate was concentrated under reduced pressure the residue was purified by silica gel column chromatography

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

Procedure: A solution of methyl 5-bromo-2-chlorobenzoate (9.23 g) in THF (50 ml) was added dropwise under ice-cooling to a suspension of lithium aluminum hydride (1.42 g) in THF (100 ml). After the completion of addition, the reaction mixture was stirred at room temperature for 45 minutes. Water (1.4 ml), 5N sodium hydroxide solution (1.4 ml) and water (4.2 ml) were sequentially added under ice-cooling to the reaction mixture. The precipitate was removed through Celite and the filtrate was concentrated under reduced pressure to obtain a title compound (7.56 g). After the completion of addition cooling to the reaction mixture The precipitate was removed through Celite the filtrate was concentrated under reduced pressure

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

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

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