Ethyl chloroformate → Ethyl 3,5-dibromoisonicotinate

Participants

Reaction Conditions

Reaction Steps

To a solution of 3,5-dibromopyridine (5 g, 21.11 mmol) in THF was added LDA (2 M in THF, 12.66 ml, 25.33 mmol) at −78° C. The mixture was stirred at −78° C. for 45 min. Then ethyl carbonochloridate (2.29 g, 21.11 mmol) was added and the mixture stirred at −78° C. for 1 hours. After reaction completed, the reaction was quenched by addition of 5 mL of saturated NH4Cl and extracted with EtOAc. The extractions were combined, washed with H2O, dried over Na2SO4 and concentrated under vacuum. The residue was purified by flash column (Eluent: PE/EtOAc=10:1), to give ethyl 3,5-dibromoisonicotinate as a yellow solid. (1.9 g, yield 29%) LCMS (M+H+) m/z: calcd 306.8. found 309.7.

Provenance & Evidence