1,2-Dichloroethane → HCID 58229473, compound

Temperature

0 °C

A dry 100 mL one neck round bottom flask was charged with 5-bromo-2-chloropyridin-3-ol (2.1454 g, 10.3 mmol), 40 mL dry DCE, and a stirbar. The slurry was fitted with an inert atmosphere inlet and cooled with an ice-water bath. To the stirring solution was added triethylamine (4.29 ml, 30.9 mmol) followed by 2-methoxyethoxymethyl chloride (1.17 ml, 10.3 mmol). The reaction was stirred at ice bath temperature for 1 h, and then at room temperature for 2 h. The reaction was cooled to 0° C. and treated with 2 mL MeOH. The slurry was filtered cold, and the solids were washed with DCE (2×50 mL). The filtrate was concentrated in vacuo and purified using 200 g SiO2 wet packed with DCE. A fraction that eluted from 500- to 1500 mL was isolated. The solvent was removed in vacuo to afford 5-bromo-2-chloro-3-((2-methoxyethoxy)methoxy)pyridine (1.28 g, 41.9% yield). 1H NMR (400 MHz, chloroform-d) δ ppm 3.38 (s, 3H) 3.55-3.59 (m, 2H) 3.86-3.89 (m, 2H) 5.36 (s, 2H) 7.71 (d, J=2.05 Hz, 1H) 8.12 (d, J=2.05 Hz, 1H). HPLC-MS: 2.04 min (>99%@215 nm; >99% @254 nm; m/z=295.9, calculated for C9H1179BrClNO3+H+=296.0; m/z=297.9, calculated for C9H1179BrClNO3+H+=298.0).

1. customThe slurry was fitted with an inert atmosphere inlet
2. temperaturecooled with an ice-water bath
3. waitat room temperature for 2 h
4. filtrationThe slurry was filtered cold
5. washthe solids were washed with DCE (2×50 mL)
6. concentrationThe filtrate was concentrated in vacuo
7. custompurified
8. washA fraction that eluted from 500- to 1500 mL
9. customwas isolated
10. customThe solvent was removed in vacuo

ORD record

ord-562c6589578f4f77aeaa691aa4a48acb

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07928140B2