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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 861003Generated: October 30, 2026

Dimethylformamide → 5-Bromopyridine-2-carbaldehyde

https://huagongshe.com/reaction/861003

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
Reactant2,5-DibromopyridineHCID 69353—
ReactantButyllithiumHCID 178418339—
Product5-Bromopyridine-2-carbaldehydeHCID 9877562—

Reaction Conditions

Temperature-78 °C

Reaction Steps

To a solution of 2,5-dibromopyridine (1.0 eq.) in Tol (O. 1M) at −78° C. was added n-BuLi (1.0Seq.). The mixture was stirred for 2 h at −78° C. then DMF (3.0 eq.) was added. The final mixture was stirred for 12 h at −78° C., quenched using saturated aqueous NH4Cl and extracted with Et2O (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. Flash chromatography (Hex:EtOAc; 9:1) afforded the title compound as an oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07153968B2
Source datasetuspto-grants-2006_12
ORD IDord-4ef352b91ace430786465ecce04b2a05
Source noteuspto-grants-2006_12