(5-bromo-2-phenylmethoxyphenyl)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: Sodium borohydride (339 mg, 8.93 mmol) was added to a solution of 2-benzyloxy-5-bromo-benzaldehyde (2.6 g, 8.93 mmol) in anhydrous ethanol (20 mL) at 0° C. The reaction was allowed to warm to room temperature and, after 3 hours, the mixture was concentrated and the residue was dissolved in ethyl acetate (50 mL) and washed with water (1×25 mL), 1N HCl solution (1×25 mL) and brine (1×25 mL). The solution was dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (8% ethyl acetate/hexane) to afford 2.58 g of the title compound as a colorless oil (98%). the mixture was concentrated the residue was dissolved in ethyl acetate (50 mL) washed with water (1×25 mL), 1N HCl solution (1×25 mL) and brine (1×25 mL) The solution was dried (Na2SO4) filtered concentrated The residue was purified by flash chromatography (8% ethyl acetate/hexane)

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 (2-benzyloxy-5-bromo-phenyl)-methanol (4.36 g, 14.87 mmol) in DCM (200 ml) cooled with ice-bath under N2 atmosphere a 1M solution of PBr3 in DCM (14.87 ml, 14.87 mmol) was added. The mixture was stirred at that temperature for 15 min and then at RT overnight. The reaction was quenched with sat. NaHCO3 solution. The organic layer was separated, washed with brine, dried (MgSO4) and evaporated to dryness. was added at RT overnight The reaction was quenched with sat. NaHCO3 solution The organic layer was separated washed with brine dried (MgSO4) evaporated to dryness

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

Procedure: To a solution of (2-benzyloxy-5-bromo-phenyl)-methanol (4.36 g, 14.87 mmol) in DCM (200 ml) cooled with ice-bath under N2 atmosphere a 1M solution of PBr3 in DCM (14.87 ml, 14.87 mmol) was added. The mixture was stirred at that temperature for 15 min and then at RT overnight. The reaction was quenched with sat. NaHCO3 solution. The organic layer was separated, washed with brine, dried (MgSO4) and evaporated to dryness. was added at RT overnight The reaction was quenched with sat. NaHCO3 solution The organic layer was separated washed with brine dried (MgSO4) evaporated to dryness

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

Procedure: A solution of 5-bromo-2-hydroxybenzylalcohol (3.677 g, 18.11 mmol) in abs. EtOH (80 ml) and NaOH (0.797 g, 19.921 mmol) was stirred under a N2 atmosphere for 20 min at RT then a solution of benzylbromide (2.15 ml, 18.11 mmol) in abs. EtOH (10 ml) was added and the mixture was stirred at RT overnight. The volatiles was removed under vacuum. The reminder was partitioned between HCl (2M aq.) and EtOAc. The organic layer was washed with brine, dried (MgSO4) and evaporated to dryness. The residue was purified by MPLC (50 g SiO2 cartridge, eluent 90% iso-hexane-10% EtOAc) yielding 4.36 g of (2-benzyloxy-5-bromo-phenyl)-methanol. The volatiles was removed under vacuum The reminder was partitioned between HCl (2M aq.) and EtOAc The organic layer was washed with brine dried (MgSO4) evaporated to dryness The residue was purified by MPLC (50 g SiO2 cartridge, eluent 90% iso-hexane-10% EtOAc)

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

Procedure: A solution of 2-benzyloxy-5-bromobenzyl alcohol (14.75 g, 50.2 mmol) in anhydrous ethyl ether (150 ml) was cooled to 4 ° C. A solution of PBr3 (13.68 g, 50 mmol) in anhydrous ether (40 ml) was added dropwise keeping the temperature below 10 ° C. The reaction was allowed to warm to ambient temperature and stirred for 1 hour. The reaction was filtered through silica gel (200 g). The silica gel was washed with ethyl ether to remove all the product. The filtrate was washed with water (1×150 ml), aqueous saturated sodium hydrogen carbonate (1×150 ml) and brine (1×150 ml). The organic layer was dried (Na2SO4) and evaporated to give 2-benzyloxy-5-bromobenzylbromide as a pale yellow oil (15.2 g, 85%) which crystallized on standing. the temperature below 10 ° C The reaction was filtered through silica gel (200 g) The silica gel was washed with ethyl ether to remove all the product The filtrate was washed with water (1×150 ml), aqueous saturated sodium hydrogen carbonate (1×150 ml) and brine (1×150 ml) The organic layer was dried (Na2SO4) evaporated