(2,3-dichlorophenyl)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: To a solution of 2,3-dichlorobenzaldehyde (Aldrich, 50 gms) in alcohol (800 mL) at room temperature was added NaBH4 (8.54 gms) and the resulting mixture stirred for 1.5 hours. The reactions: was quenched with water and the solvent evaporated in vacuo before partitioning the residue between CHCl3 and saturated NaHCO3 solution. The organic phase was washed with brine, dried over MgSO4, filtered and the solvent evaporated in vacuo to leave a white solid, 48.38 gms, mp. 87°-87.5° C. The reactions: was quenched with water the solvent evaporated in vacuo before partitioning the residue between CHCl3 and saturated NaHCO3 solution The organic phase was washed with brine dried over MgSO4 filtered the solvent evaporated in vacuo to leave a white solid, 48.38 gms, mp. 87°-87.5° C.

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

Procedure: To a solution of 2,3-dichlorobenzaldehyde (Aldrich, 50 gms) in alcohol (800 mL) at room temperature was added NaBH4 (8.54 gms) and the resulting mixture stirred for 1.5 hours. The reaction was quenched with water and the solvent evaporated in vacuo before partitioning the residue between CHCl3 and saturated NaHCO3 solution. The organic phase was washed with brine, dried over MgSO4, filtered and the solvent evaporated in vacuo to leave a white solid, 48.38 gms, mp. 87°-87.5° C. The reaction was quenched with water the solvent evaporated in vacuo before partitioning the residue between CHCl3 and saturated NaHCO3 solution The organic phase was washed with brine dried over MgSO4 filtered the solvent evaporated in vacuo to leave a white solid, 48.38 gms, mp. 87°-87.5° C.

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

Procedure: To a solution of 2,3-dichlorobenzaldehyde (Aldrich, 50 gms) in alcohol (800 mL) at room temperature was added NaBH4 (8.54 gms) and the resulting mixture stirred for 1.5 hours. The reaction was quenched with water and the solvent evaporated in vacuo before partitioning the residue between CHCl3 and saturated NaHCO3 solution. The organic phase was washed with brine, dried over MgSO4, filtered and the solvent evaporated in vacuo to leave a white solid, 48.38 gms, mp. 87°-87.5° C. The reaction was quenched with water the solvent evaporated in vacuo before partitioning the residue between CHCl3 and saturated NaHCO3 solution The organic phase was washed with brine dried over MgSO4 filtered the solvent evaporated in vacuo to leave a white solid, 48.38 gms, mp. 87°-87.5° C.

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

Procedure: To a solution of 2,3-dichlorobenzaldehyde (Aldrich, 50 gms) in alcohol (800 mL) at room temperature was added NaBH4 (8.54 gms) and the resulting mixture stirred for 1.5 hours. The reaction was quenched with water and the solvent evaporated in vacuo before partitioning the residue between CHCl3 and saturated NaHCO3 solution. The organic phase was washed with brine, dried over MgSO4, filtered and the solvent evaporated in vacuo to leave a white solid, 48.38 gms, mp. 87°-87.5° C. The reaction was quenched with water the solvent evaporated in vacuo before partitioning the residue between CHCl3 and saturated NaHCO3 solution The organic phase was washed with brine dried over MgSO4 filtered the solvent evaporated in vacuo to leave a white solid, 48.38 gms, mp. 87°-87.5° C.

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

Procedure: To a solution of 2,3-dichlorobenzaldehyde (Aldrich, 50 gms) in alcohol (800 mL) at room temperature was added NaBH4 (8.54 gms) and the resulting mixture stirred for 1.5 hours. The reaction was quenched with water and the solvent evaporated in vacuo before partitioning the residue between CHCl3 and saturated NaHCO3 solution. The organic phase was washed with brine, dried over MgSO4, filtered and the solvent evaporated in vacuo to leave a white solid, 48.38 gms, mp. 87°-87.5° C. The reaction was quenched with water the solvent evaporated in vacuo before partitioning the residue between CHCl3 and saturated NaHCO3 solution The organic phase was washed with brine dried over MgSO4 filtered the solvent evaporated in vacuo to leave a white solid, 48.38 gms, mp. 87°-87.5° C.

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

Procedure: To solution of MeOH (150 ml) containing 2,3-dichlorobenzaldehyde (20 g, 0.11 mole), cooled in ice bath, was added a solution of NaBH4 (4.54 g, 0.12 mole) in 0.2 M NaOH (15 mL) slowly over 15 min under nitrogen atmosphere. After completion of the addition, the mixture was allowed to warm up gradually to rt, and stirred for 2.5 h at rt. The reaction was quenched by cooling the mixture and pouring it slowly to ice water (˜700 mL). The mixing led to formation of white precipitates. After stirring for 30 min. the precipitates were collected on Bòcbner funnel, and the collected solid was dissolved in EtOAc (200 mL). The organic solution was washed with 0.1 M NaOH (150 mL), dried over Na2SO4, and concentrated to dryness in vacuo, yielding 2,3-dichlorobenzylalcohol as white solid (19.57 g, 97%). Rf=0.46 in EtOAc/hexane (1/3). 1H-NMR (CD3OD, 299.96 MHz: δ (ppm) 7.52-7.49 (dd, 1H), 7.45-7.42 (dd, 1H), 7.33-7.27 (t, 1H), 4.70 (s, 2H). Retention time (anal. HPLC: 10 to 70% MeCN/H2O over 6 min)=4.00 min. cooled in ice bath After completion of the addition The reaction was quenched by cooling the mixture pouring it slowly to ice water (˜700 mL) After stirring for 30 min. the precipitates were collected on Bòcbner funnel the collected solid was dissolved in EtOAc (200 mL) The organic solution was washed with 0.1 M NaOH (150 mL) dried over Na2SO4 concentrated to dryness in vacuo

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

Procedure: To a solution of 2,3-dichlorobenzaldehyde (Aldrich, 50 gms) in alcohol (800 mL) at room temperature was added NaBH4 (8.54 gms) and the resulting mixture stirred for 1.5 hours. The reaction was quenched with water and the solvent evaporated in vacuo before partitioning the residue between CHCl3 and saturated NaHCO3 solution. The organic phase was washed with brine, dried over MgSO4, filtered and the solvent evaporated in vacuo to leave a white solid, 48.38 gms, mp. 87°-87.5° C. The reaction was quenched with water the solvent evaporated in vacuo before partitioning the residue between CHCl3 and saturated NaHCO3 solution The organic phase was washed with brine dried over MgSO4 filtered the solvent evaporated in vacuo to leave a white solid, 48.38 gms, mp. 87°-87.5° C.

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

Procedure: To a solution of 2,3-dichlorobenzaldehyde (Aldrich, 50 gms) in alcohol (800 mL) at room temperature was added NaBH4 (8.54 gms) and the resulting mixture stirred for 1.5 hours. The reaction was quenched with water and the solvent evaporated in vacuo before partitioning the residue between CHCl3 and saturated NaHCO3 solution. The organic phase was washed with brine, dried over MgSO4, filtered and the solvent evaporated in vacuo to leave a white solid, 48.38 gms, mp. 87°-87.5° C. The reaction was quenched with water the solvent evaporated in vacuo before partitioning the residue between CHCl3 and saturated NaHCO3 solution The organic phase was washed with brine dried over MgSO4 filtered the solvent evaporated in vacuo to leave a white solid, 48.38 gms, mp. 87°-87.5° C.

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

Procedure: To a solution of (2,3-dichlorophenyl)methanol (75 g, 0.431 mol), in toluene (800 mL), tribromophosphine (40.7 g, 0.151 mol) was added dropwise at room temperature with stirring. Then the reaction mixture was stirred at room temperature for 2 h and concentrated. The resulting residue was neutralized with aq. NaHCO3 and extracted with DCM (300 mL*3). The organic layer was washed with brine, dried over Na2SO4, filtered and the filtrate was concentrated to provide the titled compound (84.7 g, 83%), as a deep red solid. Then the reaction mixture was stirred at room temperature for 2 h concentrated extracted with DCM (300 mL*3) The organic layer was washed with brine dried over Na2SO4 filtered the filtrate was concentrated