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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2061140Generated: November 3, 2026

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

https://huagongshe.com/reaction/2061140

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%

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 (31.9 mg, 93%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08278465B2
Source datasetuspto-grants-2012_10
ORD IDord-a42f4180dba5433abfee725f4cd2469f
Source noteuspto-grants-2012_10