Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 60907Generated: October 26, 2026

Cesium fluoride → Methyl 5-methyl-2-(pyridin-2-yl)benzoate

https://huagongshe.com/reaction/60907

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium fluorideHCID 25953—
Reactant2-(Tributylstannyl)pyridineHCID 607784—
ReactantMethyl 2-bromo-5-methylbenzoateHCID 15110996—
CatalystCopper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 24350—
CatalystHCID 178418397HCID 178418397—
SolventDimethylformamideHCID 6228—
ProductMethyl 5-methyl-2-(pyridin-2-yl)benzoateHCID 67982793—

Reaction Conditions

Temperature130 °C

Reaction Steps

A mixture of methyl 2-bromo-5-methylbenzoate (0.629 g, 2.747 mmol), 2-(tributylstannyl)pyridine (1.32 g, 3.585 mmol), CsF (0.834 g, 5.494 mmol), Pd(PPh3)4 (0.4 g, 0.27 mmol), and CuI (0.105 g, 0.549 mmol) in DMF (20 mL) was degassed for 10 min and then heated in the microwave reactor for 30 min at 130° C. The mixture was cooled and the solvent was removed in vacuo. The crude was dissolved with EtOAc and then washed with saturated NaHCO3 and dried over Na2SO4. The solvent was removed in vacuo to obtain the crude, which was purified by silica gel to obtain the title compound. ESI-MS (m/z): 228 [M+1]+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09440982B2
Source datasetuspto-grants-2016_09
ORD IDord-f5515e795507478b88057ba06393f836
Source noteuspto-grants-2016_09