(2-chloro-6-methoxyphenyl)methanol

反応条件: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: [2-Chloro-6-(methyloxy)phenyl]methanol (0.224 g, 1.30 mmol) in dry dichloromethane (4.5 ml) under nitrogen was stirred and cooled to −10° C. A solution of phosphorus tribromide (0.357 g, 1.32 mmol, Aldrich) in dry dichloromethane (4.5 ml) was added dropwise over about 40 min. The reaction temperature was slowly allowed to warm to 5° C. over about six hours then cooled to 0° C. and saturated aqueous sodium bicarbonate (5 ml) was added. The layers were separated and the aqueous phase further extracted with chloroform. The combined organic extract was dried with magnesium sulphate, filtered and solvent evaporated in vacuo to give the title compound as a slightly yellow solid (0.232 g); LCMS: (System 4) tRET=3.07 min (no MH+ detected). to warm to 5° C. over about six hours then cooled to 0° C. The layers were separated the aqueous phase further extracted with chloroform The combined organic extract was dried with magnesium sulphate filtered solvent evaporated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred solution of 2-chloro-6-(methyloxy)benzoic acid (0.252 g, 1.35 mmol, Arkpharminc) in dry THF (15 ml) at ambient temperature under nitrogen was added 1 M borane tetrahydrofuran complex (4.1 ml of solution in THF, 4.1 mmol, Aldrich) dropwise. The solution was then heated at reflux for 24 h and allowed to cool. The reaction mixture was quenched by the dropwise addition of methanol (4 ml), then heated at reflux for 30 min and allowed to cool. The solvent was removed in vacuo and the residue was partitioned between dilute aqueous ˜1M aqueous HCl and chloroform, the aqueous phase being extracted with more chloroform and the chloroform solutions being filtered through a phase separator. The combined chloroform solutions were evaporated in vacuo to give the title compound as a pale yellow solid (0.225 g); LCMS: (System 4) MH+=173, tRET=1.86 min. The solution was then heated at reflux for 24 h to cool The reaction mixture was quenched by the dropwise addition of methanol (4 ml) heated at reflux for 30 min to cool The solvent was removed in vacuo the residue was partitioned between dilute aqueous ˜1M aqueous HCl and chloroform the aqueous phase being extracted with more chloroform the chloroform solutions being filtered through a phase separator The combined chloroform solutions were evaporated in vacuo