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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2355272Generated: November 1, 2026

Sodium Azide → Methyl 4-(azidomethyl)-2-chlorobenzoate

https://huagongshe.com/reaction/2355272

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium AzideHCID 33557—
ReactantMethyl 4-(bromomethyl)-2-chlorobenzoateHCID 22072833—
SolventDimethylformamideHCID 6228—
ProductMethyl 4-(azidomethyl)-2-chlorobenzoateHCID 5746122689.1%

Reaction Conditions

Temperature50 °C

Reaction Steps

Add sodium azide (2.44 g, 37.49 mmol) to crude 4-bromomethyl-2-chloro-benzoic acid methyl ester (7.6 g, 28.84 mmol) in anhydrous dimethylformamide (100 mL) at room temperature under argon gas. Stir the reaction mixture at 50° C. overnight. Quench the reaction mixture with water and extract with ether (3×). Combine the organic layers, wash with brine, dry over sodium sulfate, and concentrate to provide the crude product (5.8 g, 25.7 mmol).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07754742B2
Source datasetuspto-grants-2010_07
ORD IDord-30dd83ab2ae8426a8bc1992b23881f86
Source noteuspto-grants-2010_07