Methanol → Methyl 2-(5-bromopyridin-3-yl)acetate

To a solution of (5-bromo-pyridin-3-yl)-acetic acid (4.2 g, 20 mmol) in methanol (50 mL) was added thionyl chloride (4.4 mL, 60 mmol) slowly at 0° C. After the addition, the reaction mixture was warmed up and heated to reflux temperature for 2 hours. After cooling back to room temperature, the reaction mixture was concentrated in vacuo and the residue was re-dissolved in EtOAc (250 mL) and washed with aq. NaHCO3 solution and brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo to give a crude product (4.6 g, quant.) as light yellow solid. MS: 230.1 & 232.0 (M+H+).

1. additionAfter the addition
2. temperaturethe reaction mixture was warmed up
3. temperatureheated
4. temperatureto reflux temperature for 2 hours
5. concentrationthe reaction mixture was concentrated in vacuo
6. dissolutionthe residue was re-dissolved in EtOAc (250 mL)
7. washwashed with aq. NaHCO3 solution and brine
8. dry with materialThe organic layer was dried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-6483e90d551a4697844594f01a0e0eb9

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133158B2