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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2253355Generated: November 1, 2026

Toluene → HCID 68435567, compound

https://huagongshe.com/reaction/2253355

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantVeratrylamineHCID 79832—
ReactantHCID 9924988HCID 9924988—
ReactantSodium t-butoxideHCID 23676156—
Catalystpalladium(II) acetateHCID 167845—
CatalystBinap, (A+-)-HCID 634876—
SolventEthyl AcetateHCID 8857—
ProductHCID 68435567HCID 6843556764.5%

Reaction Conditions

Temperature80 °C

Reaction Steps

Under a nitrogen atmosphere, to toluene (1 mL) were added 5-bromo-2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran (100 mg) and 3,4-dimethoxybenzylamine (56 mg), then palladium acetate (0.3 mg) and (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (2.7 mg), and further sodium tert-butoxide (37.5 mg). The mixture was stirred at 80° C. for 17 hours. Ethyl acetate was added to the reaction mixture, insoluble materials were filtered and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, which was eluted with ethyl acetate-n-hexane [1:4], to obtain the title compound (80 mg, 64.5%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07323577B2
Source datasetuspto-grants-2008_01
ORD IDord-1e949b4668e145559bb2e3ce31d2cd0d
Source noteuspto-grants-2008_01