Sodium Hydroxide → 3-Bromo-5-(chloromethyl)pyridine

To a solution of (5-bromopyridin-3-yl)methanol (3 g, 16.0 mmol) in DCM (15 mL) cooled to 0° C. was added thionylchloride (7.59 g, 63.8 mmol) dropwise and the reaction mixture was stirred at room temperature over night. The mixture was poured onto ice/water (20 mL), basified with NaOH conc. (8 mL) and extracted with EtOAc (2×50 mL). Combined organics were dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 40% EtOAc-Heptane gradient to give the title compound (3.08 g, 93%) as a white solid. MS: 206.0, 207.9 (M+H+).

1. additionThe mixture was poured onto ice/water (20 mL)
2. extractionextracted with EtOAc (2×50 mL)
3. dry with materialCombined organics were dried over Na2SO4
4. filtrationfiltered
5. customevaporated to dryness
6. customThe residue was purified by silica gel flash chromatography
7. washeluting with a 0 to 40% EtOAc-Heptane gradient

ORD record

ord-921d1432379b42479dd93a6de7f66998

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09260408B2