Phosphorus tribromide → HCID 86680628, compound

To a stirred solution of 1-(5-(4-methoxyphenyl)pyridin-2-yl)ethanol (0.2 g, 0.8 mmol) in chloroform (4 mL) was added PBr3 (0.3 mL, 1.3 mmol) at 0° C. and the reaction was stirred at 0° C. to rt for about 1 h. The reaction mixture was quenched with saturated NaHCO3 solution (10 mL) and extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with brine solution (10 mL), the organic layer was dried over Na2SO4 and concentrated under vacuum to obtain crude product. The crude product was purified by flash chromatography (silica gel, 60-120μ) using 10% ethyl acetate in hexane eluent to provide 2-(1-bromoethyl)-5-(4-methoxyphenyl)pyridine (0.15 g, 58% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.76 (d, 1H), 7.84 (dd, 1H), 7.51 (dd, 3H), 7.01 (d, 2H), 5.32-5.26 (m, 1H), 3.86 (s, 3H), 2.11 (d, 3H), LC-MS m/z calcd for [M+H]+ 292.0. found 292.3.

1. customThe reaction mixture was quenched with saturated NaHCO3 solution (10 mL)
2. extractionextracted with ethyl acetate (2×100 mL)
3. washThe combined organic extracts were washed with brine solution (10 mL)
4. dry with materialthe organic layer was dried over Na2SO4
5. concentrationconcentrated under vacuum
6. customto obtain crude product
7. customThe crude product was purified by flash chromatography (silica gel, 60-120μ)

ORD record

ord-e2d8f825b3ad4379a8de680131802b8c

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09199975B2