Hydrochloric Acid → (2-Chloropyridin-4-yl)methanol

To a stirred solution of 2-chloroisonicotinic acid (3.15 g, 20 mmol) in anhydrous THF (40 ml) cooled in an ice bath, was added borane-methyl sulfide complex (6 mL, 60 mmol). After 1 hr, the mixture was stirred for 48 hr at room temperature. The mixture was cooled in an ice bath and conc. HCl (30 ml) was added and stirred for 30 min. The mixture was then basified by addition of 50% aqueous NaOH (30 ml). The product was extracted with dichloromethane, dried with anhydrous potassium carbonate, filtered, and evaporated in vacuo. The crude product was purified by silica gel column chromatography (eluent, ether:hexane (5:1)) to afford 172 g (60%) of 2-chloro-4-pyridinemethanol as a white solid. m.p. 77-79° C.; 1H NMR (200 MHz, CDCl3) δ 2.97 (1H, br. s), 4.74 (2H, s), 7.20 (1H, d, J=5.7 Hz), 7.36 (1H, s), 8.28 (1H, d, J=5.7 Hz).

1. additionwas added borane-methyl sulfide complex (6 mL, 60 mmol)
2. temperatureThe mixture was cooled in an ice bath
3. stirringstirred for 30 min
4. extractionThe product was extracted with dichloromethane
5. dry with materialdried with anhydrous potassium carbonate
6. filtrationfiltered
7. customevaporated in vacuo
8. customThe crude product was purified by silica gel column chromatography (eluent, ether:hexane (5:1))

ORD record

ord-a1cefcc5119840f29ddf09ec610d3f14

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08106064B2