Methanol → HCID 67308872, compound

To a solution of 5-fluoro-2-iodo-3-methyl-benzoic acid methyl ester (11.2 g) in dichloromethane (80 mL) was added dropwise over 25 minutes diisobutyl aluminium hydride (113 mL, 1.02 mol/L hexane solution) at −78° C., and the mixture was stirred at the same temperature for 30 minutes. To the reaction mixture was added dropwise methanol (10 mL) at the same temperature, and the mixture was stirred for 10 minutes. To the reaction mixture was added a saturated potassium sodium tartrate tetrahydrate aqueous solution (300 mL) under ice-cooling, and the mixture was stirred for 30 minutes. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was washed with hexane to give (5-fluoro-2-iodo-3-methyl-phenyl)methanol (7.15 g). To a suspension of the obtained compound (7.15 g) in chloroform (53 mL) and acetone (5.2 mL) was added manganese dioxide, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was filtered through a Celite pad, and the filtrate was concentrated. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=0-15%) to give the title compound (3.54 g).

1. stirringthe mixture was stirred for 10 minutes
2. temperaturecooling
3. stirringthe mixture was stirred for 30 minutes
4. extractionThe reaction mixture was extracted with ethyl acetate
5. washThe organic layer was washed with brine
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. washThe residue was washed with hexane

ORD record

ord-e0ef9d5069ed4a78a26b304115f7c3b7

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08263622B2