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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 252815Generated: October 25, 2026

Acetone → HCID 59736875, compound

https://huagongshe.com/reaction/252815

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetoneHCID 180—
ReactantAllyl AlcoholHCID 7858—
ReactantTri-o-tolylphosphineHCID 80271—
Reactant5-Bromo-2-nitroanilineHCID 5314766—
SolventDimethylformamideHCID 6228—
SolventDiisopropylethylamineHCID 81531—
ProductHCID 59736875HCID 5973687518.3%

Reaction Conditions

Temperature120 °C

Reaction Steps

A solution of bromoarene 2 (1.544 g, 7.11 mmol) (or any haloarene of choice); tri-o-tolyl-phosphine (280 mg; 0.9 mmol) and trkdibenzylidene acetone)dipalladium(0) (280 mg; 0.3 mmol) in N,N-dimethylformamide (6 mL) and ethyl diisopropyl amine (3 mL) was treated with prop-2-en-1-ol (3 mL, 40 mmol) (or any alken-1-ol of choice, 6 eq.) and the solution was stirred at 120° C. for 3 h under nitrogen. The reaction mixture was concentrated under high vacuum and the residue was purified by flash chromatography (eluent 5% MeOH in dichloromethane) to afford the aldehyde 80 (253 mg, 18% yield).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07868205B2
Source datasetuspto-grants-2011_01
ORD IDord-46531cf331804d6badbde7637ca3970e
Source noteuspto-grants-2011_01