(4-fluoro-2-phenylmethoxyphenyl)methanol

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

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

Procedure: A mixture of 2-(benzyloxy)-4-fluorobenzyl alcohol (6.54 g) and manganese(IV) oxide (9.04 g) in chloroform (70 ml) was refluxed and stirred for 2 hr. The insoluble material was removed by filtration and washed with chloroform. The filrate was evaporated and the residue (6.7 g) was chromatographed over silica gel (90 g) eluting with a mixture of hexane and dichloromethane (5:1) to dichloromethane to give a colorless oil of 2-(benzyloxy)-4-fluorobenzaldehyde (3.8 g, 59%). was refluxed The insoluble material was removed by filtration washed with chloroform The filrate was evaporated the residue (6.7 g) was chromatographed over silica gel (90 g) eluting with a mixture of hexane and dichloromethane (5:1) to dichloromethane

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

Procedure: A mixture of the product from step (iii) (1.06 g), methane sulphonyl chloride (0.351 ml) and triethylamine (0.636 ml) in DCM (20 ml) was stirred at RT for 2 h. The mixture was partitioned between water/DCM, the organics separated, dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with isohexane/DCM 1:1, yield 0.7 g. The mixture was partitioned between water/DCM the organics separated, dried evaporated under reduced pressure The residue was purified by chromatography on silica eluting with isohexane/DCM 1:1, yield 0.7 g

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

Procedure: A mixture of the product from step (iii) (1.06 g), methane sulphonyl chloride (0.351 ml) and triethylamine (0.636 ml) in DCM (20 ml) was stirred at RT for 2 h. The mixture was partitioned between water/DCM, the organics separated, dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with isohexane/DCM 1:1, yield 0.7 g. The mixture was partitioned between water/DCM the organics separated, dried evaporated under reduced pressure The residue was purified by chromatography on silica eluting with isohexane/DCM 1:1, yield 0.7 g

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

Procedure: Sodium borohydride (0.223 g) was added to a solution of the product from step (ii) (1.07 g) in dry ethanol (30 ml) and the mixture was stirred at RT overnight. The mixture was partitioned between 2M hydrochloric acid/ethyl acetate, the organics separated, dried and evaporated under reduced pressure, yield 1.08 g. The mixture was partitioned between 2M hydrochloric acid/ethyl acetate the organics separated, dried evaporated under reduced pressure, yield 1.08 g

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

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

Procedure: A mixture of 2-(benzyloxy)-4-fluorobenzyl alcohol (6.54 g) and manganese(IV) oxide (9.04 g) in chloroform (70 ml) was refluxed and stirred for 2 hr. The insoluble material was removed by filtration and washed with chloroform. The filrate was evaporated and the residue (6.7 g) was chromatographed over silica gel (90 g) eluting with a mixture of hexane and dichloromethane (5:1) to dichloromethane to give a colorless oil of 2-(benzyloxy)-4-fluorobenzaldehyde (3.8 g, 59%). was refluxed The insoluble material was removed by filtration washed with chloroform The filrate was evaporated the residue (6.7 g) was chromatographed over silica gel (90 g) eluting with a mixture of hexane and dichloromethane (5:1) to dichloromethane

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

Procedure: A mixture of the product from step (iii) (1.06 g), methane sulphonyl chloride (0.351 ml) and triethylamine (0.636 ml) in DCM (20 ml) was stirred at RT for 2 h. The mixture was partitioned between water/DCM, the organics separated, dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with isohexane/DCM 1:1, yield 0.7 g. The mixture was partitioned between water/DCM the organics separated, dried evaporated under reduced pressure The residue was purified by chromatography on silica eluting with isohexane/DCM 1:1, yield 0.7 g

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

Procedure: Sodium borohydride (0.223 g) was added to a solution of the product from step (ii) (1.07 g) in dry ethanol (30 ml) and the mixture was stirred at RT overnight. The mixture was partitioned between 2M hydrochloric acid/ethyl acetate, the organics separated, dried and evaporated under reduced pressure, yield 1.08 g. The mixture was partitioned between 2M hydrochloric acid/ethyl acetate the organics separated, dried evaporated under reduced pressure, yield 1.08 g

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