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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2105267Generated: November 2, 2026

Dimethylformamide → 5-Bromopyridine-2-carbaldehyde

https://huagongshe.com/reaction/2105267

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantAmmonium ChlorideHCID 25517—
Reactant2,5-DibromopyridineHCID 69353—
ReactantButyllithiumHCID 178418339—
SolventTolueneHCID 1140—
Product5-Bromopyridine-2-carbaldehydeHCID 9877562—

Reaction Conditions

Temperature-10 °C

Reaction Steps

To a solution of 2,5-dibromopyridine (1 g) in toluene (50 mL) at −78° C. was slowly added 2.5M n-BuLi (2 mL). The reaction mixture was stirred for 2 h, then DMF (0.5 mL) was added. The solution was stirred for 1 h at −78° C., then warmed to −10° C. Saturated NH4Cl (10 mL) was added and the mixture was allowed to warm to room temperature. The two phases were partitioned and the organic layer dried over sodium sulfate and the solvent concentrated to dryness to afford 0.432 g of the title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07579353B2
Source datasetuspto-grants-2009_08
ORD IDord-d5741d4b462644598c47a1f95df2ed83
Source noteuspto-grants-2009_08