Ethanol → Ethyl 5,6-Dichloronicotinate

Participants

Reaction Steps

A solution of 5,6-dichloronicotinic acid (5.0 g, 26.0 mmol) in dry ethanol (300 mL) and chlorotrimethylsilane (33 mL, 10 eq.) is stirred at rt for 16 h. The solvent is evaporated, the residue dissolved in diethyl ether (200 mL) and washed with a solution of sat. aq. Na2CO3 (75 mL) and brine (50 mL). The org. phase is dried over Na2SO4, filtered and evaporated to give 5,6-dichloronicotinic acid ethyl ester (5.8 g) as a solid; LC-MS: tR=0.96 min, [M+1]+=219.93.

Provenance & Evidence