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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1466009Generated: October 31, 2026

Toluene → 5-Allyl-2,1,3-benzoxadiazole

https://huagongshe.com/reaction/1466009

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantAllyltributylstannaneHCID 90628—
ReactantLithium ChlorideHCID 433294—
Reactant5-Bromo-2,1,3-benzoxadiazoleHCID 2776298—
CatalystHCID 178418397HCID 178418397—
SolventEthyl AcetateHCID 8857—
Product5-Allyl-2,1,3-benzoxadiazoleHCID 59568714—

Reaction Conditions

Temperature110 °C

Reaction Steps

To a 250 mL flask charged with 5-Bromo-2,1,3-benzoxadiazole (5.0 g, 25 mmol), Palladium Tetrakis (0.87 g, 0.75 mmol), and lithium chloride (2.1 g, 50 mmol) was added Allyl Tri-n-butyltin (10 g, 30 mmol) and toluene (100 mL). The mixture was attached to a reflux condenser, sealed and purged with nitrogen. The reaction was heated to 110° C. for 2 hours. TLC showed good and complete reaction. The reaction was diluted with EtOAc, washed with brine, concentrated and purified by silica gel chromatography.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08999990B2
Source datasetuspto-grants-2015_04
ORD IDord-6554cabd3a8c4d4d81472f4ed1bad63a
Source noteuspto-grants-2015_04