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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2387752Generated: October 30, 2026

Dimethylformamide → 5-Bromo-2-fluoro-3-methoxypyridine

https://huagongshe.com/reaction/2387752

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
Reactant5-Bromo-3-methoxy-2-nitropyridineHCID 817774—
ReactantTetrabutylammonium FluorideHCID 2724141—
SolventWaterHCID 962—
Product5-Bromo-2-fluoro-3-methoxypyridineHCID 58626691—

Reaction Conditions

Temperature70 °C

Reaction Steps

Tetrabutyl ammonium fluoride (1.0 M THF solution: 3.9 ml) was added to a DMF (5 ml) solution of 5-bromo-3-methoxy-2-nitropyridine (CAS No. 152684-26-9) (450 mg), and the obtained mixture was stirred at 70° C. for 72 hours. The reaction solution was cooled to room temperature. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-heptane:ethyl acetate=10:1 to 2:1), so as to obtain the title compound (258 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08268848B2
Source datasetuspto-grants-2012_09
ORD IDord-3788acb020a14ad0a818a7b767ddb9ed
Source noteuspto-grants-2012_09