methyl 4-bromo-3-(hydroxymethyl)benzoate

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a −78° C. solution of dimethyl 4-bromoisophthalate (21.0 g, 77 mmol)(commercially available from Maybridge) in THF (100 mL) was slowly added diisobutylaluminum hydride (269 mL, 269 mol, 1.0 M solution in hexane, commercially available from Sigma-Aldrich, St. Louis, Mo., USA) over 20 minutes. After stirring at −78° C. for 3 hours, the resulting mixture was treated with MeOH. Organic solvents were removed under reduced pressure and the residue was redissolved in EtOAc and washed with 1.0 N HCl. After removal of organic solvents under reduced pressure, purification of the residue through silica gel chromatography with 0-35% EtOAc in hexanes as eluents afforded 132.1 (7.1 g, 38%). To a −78° C. Organic solvents were removed under reduced pressure the residue was redissolved in EtOAc washed with 1.0 N HCl After removal of organic solvents under reduced pressure, purification of the residue through silica gel chromatography with 0-35% EtOAc in hexanes as eluents

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a −78° C. solution of dimethyl 4-bromoisophthalate (21.0 g, 77 mmol)(commercially available from Maybridge) in THF (100 mL) was slowly added diisobutylaluminum hydride (269 mL, 269 mol, 1.0 M solution in hexane, commercially available from Sigma-Aldrich, St. Louis, Mo., USA) over 20 minutes. After stirring at −78° C. for 3 hours, the resulting mixture was treated with MeOH. Organic solvents were removed under reduced pressure and the residue was redissolved in EtOAc and washed with 1.0 N HCl. After removal of organic solvents under reduced pressure, purification of the residue through silica gel chromatography with 0-35% EtOAc in hexanes as eluents afforded 132.1 (7.1 g, 38%). To a −78° C. Organic solvents were removed under reduced pressure the residue was redissolved in EtOAc washed with 1.0 N HCl After removal of organic solvents under reduced pressure, purification of the residue through silica gel chromatography with 0-35% EtOAc in hexanes as eluents

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a −78° C. solution of dimethyl 4-bromoisophthalate (21.0 g, 77 mmol)(commercially available from Maybridge) in THF (100 mL) was slowly added diisobutylaluminum hydride (269 mL, 269 mol, 1.0 M solution in hexane, commercially available from Sigma-Aldrich, St. Louis, Mo., USA) over 20 minutes. After stirring at −78° C. for 3 hours, the resulting mixture was treated with MeOH. Organic solvents were removed under reduced pressure and the residue was redissolved in EtOAc and washed with 1.0 N HCl. After removal of organic solvents under reduced pressure, purification of the residue through silica gel chromatography with 0-35% EtOAc in hexanes as eluents afforded 132.1 (7.1 g, 38%). To a −78° C. Organic solvents were removed under reduced pressure the residue was redissolved in EtOAc washed with 1.0 N HCl After removal of organic solvents under reduced pressure, purification of the residue through silica gel chromatography with 0-35% EtOAc in hexanes as eluents