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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1046811Generated: November 1, 2026

Imidazole → 4-(((tert-Butyldimethylsilyl)oxy)methyl)-2-chloro-3-fluoropyridine

https://huagongshe.com/reaction/1046811

Reaction equation

Participants

RoleNameHCIDCharge
ReactantImidazoleHCID 795—
ReactantDichloromethaneHCID 6344—
Reactanttert-Butyldimethylsilyl chlorideHCID 28928—
Reactant(2-Chloro-3-Fluoropyridin-4-Yl)MethanolHCID 54759140—
SolventDimethylformamideHCID 6228—
Product4-(((tert-Butyldimethylsilyl)oxy)methyl)-2-chloro-3-fluoropyridineHCID 5913917793.3%

Reaction Steps

A mixture of (2-chloro-3-fluoropyridin-4-yl)-methanol (200 mg, 1.24 mmol), imidazole (253 mg, 3.72 mmol) and tert-butyldimethylchlorosilane (373 mg, 2.48 mmol) in DMF was stirred at room temperature for 2 hours. Methylene chloride was then added to the reaction solution, and the solution was washed with saturated saline. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduced pressure. The resultant residue was purified by silica gel column chromatography to yield the title compound (319 mg, 93%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08569378B2
Source datasetuspto-grants-2013_10
ORD IDord-2339fb3a1dff4d7e88109e9c29775343
Source noteuspto-grants-2013_10