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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 339982Generated: October 26, 2026

Methyl iodide → Methyl 5-bromo-3-methylpicolinate

https://huagongshe.com/reaction/339982

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl iodideHCID 6328—
ReactantPotassium CarbonateHCID 11430—
Reactant5-Bromo-3-methylpyridine-2-carboxylic acidHCID 45789779—
SolventDimethylformamideHCID 6228—
ProductMethyl 5-bromo-3-methylpicolinateHCID 4578978783.3%

Reaction Conditions

Temperature80 °C

Reaction Steps

To a solution 5-bromo-3-methylpyridine-2-carboxylic acid (2.6 g, 12 mmol) in N,N-dimethylformamide (20.0 mL) was added potassium carbonate (4.99 g, 36.1 mmol) and methyl iodide (1.50 mL, 24.1 mmol) and the reaction was stirred 80° C. for 40 min. The reaction mixture was partitioned with EtOAc and water. The organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated to afford 2.3 g (83% yield) of the desired product as a yellow solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08895571B2
Source datasetuspto-grants-2014_11
ORD IDord-4b3aceba0be74e91ad8e95f6d994077f
Source noteuspto-grants-2014_11