Phosphorus tribromide → 3-(Bromomethyl)-2-chloropyridine

To a stirred solution of the title compound of Step A (5.50 g, 38.3 mmol) in CH2Cl2 (60 mL) at 0° C. under N2 was added phosphorus tribromide (3.60 mL, 38.3 mmol). The solution was allowed to warm to room temperature overnight. The solution was poured into ice water and the aqueous layer was extracted with CHCl3. The combined organic extracts were washed with water, 5% NaHCO3, and saturated aqueous NACl, dried over MgSO4 and concentrated in vacuo to a yellow oil. Purification by flash chromatography during with 20% ethyl acetate/hexanes afforded the title compound of Step B as a white solid (5.06 g). 1H NMR (CDCl3, 300 MHz) δ8.34 (dd, 1H), 7.80 (dd,1H), 7.26 (dd, 1H), 4.56 (s,2H).

1. extractionthe aqueous layer was extracted with CHCl3
2. washThe combined organic extracts were washed with water, 5% NaHCO3, and saturated aqueous NACl
3. dry with materialdried over MgSO4
4. concentrationconcentrated in vacuo to a yellow oil
5. customPurification by flash chromatography during with 20% ethyl acetate/hexanes

ORD record

ord-17cddcce34f243aab3fed6931af19494

Source dataset

uspto-grants-1998_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05739326