Methanol → methyl 4-bromo-3-(hydroxymethyl)benzoate

Temperature

-78 °C

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%).

1. customTo a −78° C.
2. customOrganic solvents were removed under reduced pressure
3. dissolutionthe residue was redissolved in EtOAc
4. washwashed with 1.0 N HCl
5. customAfter removal of organic solvents
6. customunder reduced pressure, purification of the residue through silica gel chromatography with 0-35% EtOAc in hexanes as eluents

ORD record

ord-5485a2fc3de7450da3fae4918c561883

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08748462B2