Thionyl Chloride → HCID 23089924, compound

To a solution of 2-chloro-4-(3-fluorophenyl)nicotinic acid (8.37 g) in tetrahydrofuran (70 ml) was added thionyl chloride (11.9 g), and the mixture was heated under reflux for 2.5 hrs. The reaction mixture was concentrated and the obtained residue was dissolved in tetrahydrofuran (50 ml). This solution was added dropwise to an ice-cooled aqueous sodium borohydride (4.58 g) solution, and the mixture was stirred at room temperature for 3 hrs. The reaction mixture was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography to give [2-chloro-4-(3-fluorophenyl)pyridin-3-yl]methanol (3.07 g) as a colorless oil.

1. temperaturethe mixture was heated
2. temperatureunder reflux for 2.5 hrs
3. concentrationThe reaction mixture was concentrated
4. dissolutionthe obtained residue was dissolved in tetrahydrofuran (50 ml)
5. additionThis solution was added dropwise to an ice-
6. temperaturecooled aqueous sodium borohydride (4.58 g) solution
7. extractionThe reaction mixture was extracted with ethyl acetate
8. washthe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
9. dry with materialdried over anhydrous magnesium sulfate
10. customThe solvent was evaporated
11. customthe residue was purified by silica gel column chromatography

ORD record

ord-8a8ed78fadea452faf83486448afe27d

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07625887B2