(3-bromo-5-methoxyphenyl)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:; See reaction.notes.procedure_details.

Procedure: 11 Grams (51 mmole) of 3-bromo-5methoxy benzyl alcohol was dissolved in 100 ml methylene chloride and cooled in an ice-bath. 2.0 ml (20 mmole) of phosphorus tribromide was added dropwise to this solution at room temperature, and the mixture was allowed to stir for 10 minutes. Saturated sodium bicarbonate solution was then added, and the mixture was extracted with ether and washed with sodium bicarbonate solution. Evaporation of the ether yielded 12 grams of 3-Bromo-5-methoxy-benzyl bromide as a white solid. cooled in an ice-bath the mixture was extracted with ether washed with sodium bicarbonate solution Evaporation of the ether

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

Procedure: 11 Grams (51 mmole) of 3-bromo-5methoxy benzyl alcohol was dissolved in 100 ml methylene chloride and cooled in an ice-bath. 2.0 ml (20 mmole) of phosphorus tribromide was added dropwise to this solution at room temperature, and the mixture was allowed to stir for 10 minutes. Saturated sodium bicarbonate solution was then added, and the mixture was extracted with ether and washed with sodium bicarbonate solution. Evaporation of the ether yielded 12 grams of 3-Bromo-5-methoxy-benzyl bromide as a white solid. cooled in an ice-bath the mixture was extracted with ether washed with sodium bicarbonate solution Evaporation of the ether

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

Procedure: 13.5 Grams (55 mmole)) Methyl 3-bromo-5-methoxybenzoate was dissolved in ether and cooled in an ice bath. 33 ml of 1M lithium aluminum hydride was added dropwise. The reaction mix was then quenched cautiously by addition of sodium sulfate decahydrate, then water, and solid residue was removed by filtration. The ether was separated and evaporated under reduced pressure to give 11 gms of 3-bromo-5-methoxy benzyl alcohol as a white solid. cooled in an ice bath The reaction mix was then quenched cautiously by addition of sodium sulfate decahydrate water, and solid residue was removed by filtration The ether was separated evaporated under reduced pressure

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

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

Procedure: Triphenylphosphine (28 g; KANTO) was added to a dichloromethane (150 mL) solution of Intermediate 1 (22.05 g) with ice cooling, the resulting mixture was stirred for approx. 10 minutes followed by the addition of N-bromosuccinimide (20 g; TCI), and the resulting mixture was stirred at room temperature for 13 hours and 30 minutes. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography (n-hexane/ethyl acetate) to give the title compound (23.94 g). the resulting mixture was stirred at room temperature for 13 hours and 30 minutes The solvent was evaporated under reduced pressure the residue was purified by column chromatography (n-hexane/ethyl acetate)

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

Procedure: NaBH4 (3.85 g; WAKO) was added to an ethanol (80 mL) and THF (20 mL) mixture solution of 3-bromo-5-methoxybenzaldehyde (22 g) with ice cooling and the resulting mixture was stirred at room temperature for 3 hours. The resulting mixture was poured into ice water (300 mL) and ethyl acetate (300 mL) was added thereto to extract the mixture with and the organic layer was washed with saturated aqueous sodium bicarbonate solution (300 mL) and then dried. The solvent was evaporated under reduced pressure to give the title compound (22.05 g). was added to extract the mixture with and the organic layer was washed with saturated aqueous sodium bicarbonate solution (300 mL) dried The solvent was evaporated under reduced pressure

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

Procedure: The product from step (iii) (5.38 g) was dissolved in dry DCM (50 ml) and dry DMF (2.3 ml) added followed by thionyl chloride (2.17 ml). The reaction mixture was stirred at RT overnight, and then diluted with aqueous sodium hydrogen carbonate, extracted with DCM, dried (MgSO4) and evaporated under reduced pressure to give an oil. The oil was dissolved in DMF (20 ml), sodium cyanide (1.30 g) was added and stirred at RT overnight. The reaction mixture was diluted with water, extracted with ether, dried (MgSO4) and evaporated under reduced pressure. The residue was purified by flash column chromatography (eluent 1:2 ether/isohexane) to give the subtitle compound (4.50 g). extracted with DCM dried (MgSO4) evaporated under reduced pressure to give an oil stirred at RT overnight extracted with ether dried (MgSO4) evaporated under reduced pressure The residue was purified by flash column chromatography (eluent 1:2 ether/isohexane)

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

Procedure: Lithium aluminium hydride (1M in THF, 22.07 ml) was added dropwise to a stirred solution of the product of step (ii) (5.1 g) in THF (50 ml) at 0° C. and stirred at RT overnight. The reaction was quenched in 2M HCl, extracted with ether, dried (MgSO4) and evaporated under reduced pressure to give an oil, which was purified by flash column chromatography (eluent 1:1 isohexane/diethylether) to give the subtitle compound (5.38 g). The reaction was quenched in 2M HCl extracted with ether dried (MgSO4) evaporated under reduced pressure to give an oil, which was purified by flash column chromatography (eluent 1:1 isohexane/diethylether)

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

Procedure: 11 Grams (51 mmole) of 3-bromo-5methoxy benzyl alcohol was dissolved in 100 ml methylene chloride and cooled in an ice-bath. 2.0 ml (20 mmole) of phosphorus tribromide was added dropwise to this solution at room temperature, and the mixture was allowed to stir for 10 minutes. Saturated sodium bicarbonate solution was then added, and the mixture was extracted with ether and washed with sodium bicarbonate solution. Evaporation of the ether yielded 12 grams of 3-Bromo-5-methoxy-benzyl bromide as a white solid. cooled in an ice-bath the mixture was extracted with ether washed with sodium bicarbonate solution Evaporation of the ether