Ethanol → Ethyl 5,6-Dichloronicotinate

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Reaction Steps

A solution of 5,6-dichloronicotinic acid (5.0 g, 26 mmol) in dry EtOH (300 mL) and chlorotrimethylsilane (33 mL, 10 eq.) is stirred at rt for 16 h. The solvent is evaporated, the residue dissolved in 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