Diisobutylaluminum hydride → [4-Bromo-2-(methanesulfonyl)phenyl]methanol

To a stirring solution of methyl 4-bromo-2-(methylsulfonyl)benzoate (1000 mg, 3.41 mmol) in THF (20 mL) at −78° C. was added DIBAL-H solution (1.0 M in hexanes, 7.50 ml, 2.20 equiv.) dropwise. The mixture was stirred for 15 min and then gradually warmed to room temperature and stirred for another 4 hour. LCMS indicated clean conversion of the starting material to the product. The reaction was quenched with sodium bicarbonate, and then concentrated to dryness. The resulting solids were stirred with DCM (100 ml) for 1 hour and then filtered. The solids were rinsed with EtOAc until the rinse was free of product. The combined filtrate were dried over sodium sulfate, concentrated to dryness to give the desired product (788 mg)

1. stirringstirred for another 4 hour
2. customThe reaction was quenched with sodium bicarbonate
3. concentrationconcentrated to dryness
4. stirringThe resulting solids were stirred with DCM (100 ml) for 1 hour
5. filtrationfiltered
6. washThe solids were rinsed with EtOAc until the rinse
7. dry with materialThe combined filtrate were dried over sodium sulfate
8. concentrationconcentrated to dryness

ORD record

ord-817cd5d0e2644f67ac271e2eb6962956

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916593B2