Ethanol → Ethyl 5,6-Dichloronicotinate

To a solution of 5,6-dichloronicotinic acid (20.01 g, 104 mmol) in EtOH (500 mL) at 20° C. was added chlorotrimethylsilane (132 mL, 1042 mmol). The reaction was stirred for 72 hours. The reaction mixture was then concentrated and diluted with EtOAc (500 mL), and washed with saturated NaHCO3 (2×100 mL) and brine (100 mL). The organic was then dried (Na2SO4) and concentrated under reduced pressure to give final crude product (21.25 g). LCMS m/z 220.1 (M+H)+, Rt 0.94 min.

1. concentrationThe reaction mixture was then concentrated
2. additiondiluted with EtOAc (500 mL)
3. washwashed with saturated NaHCO3 (2×100 mL) and brine (100 mL)
4. dry with materialThe organic was then dried (Na2SO4)
5. concentrationconcentrated under reduced pressure

ORD record

ord-5a45f9597fb941b9ae778f44080a3dfb

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434719B2