Water → 4-Chloro-2-nitrobenzyl alcohol

Under nitrogen atmosphere, a solution of 4-chloro-2-nitro-benzoic acid (4.00 g) in THF (15 mL) was cooled to 0° C., and thereto was added dropwise dimethylsulfideborane (2.51 mL), and the mixture was stirred at room temperature for 16 hours. To the reaction solution were added water and a saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated brine, and dried over MgSO4. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column (hexane/ethyl acetate=2/1) to give (4-chloro-2-nitrophenyl)methanol (1.32 g, 36%).

1. additionwas added dropwise dimethylsulfideborane (2.51 mL)
2. extractiona saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate
3. washThe organic layer was washed with a saturated brine
4. dry with materialdried over MgSO4
5. customThe solvent was evaporated under reduced pressure
6. customthe residue was purified by silica gel column (hexane/ethyl acetate=2/1)

ORD record

ord-cb9cf8c034b54b379e07edc1053210e0

Source dataset

uspto-grants-2004_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06759429B2