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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 61831Erstellt: 24. Oktober 2026

Toluene → 3-Chloro-9-bromo-8-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy)-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one

https://huagongshe.com/de/reaction/61831

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktTolueneHCID 1140—
EduktTriphenylphosphineHCID 11776—
Eduktethyl N-ethoxycarbonyliminocarbamateHCID 220568—
Edukt(R)-SolketalHCID 736056—
Edukt9-Bromo-3-chloro-8-hydroxy-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-oneHCID 66834693—
LösungsmittelTetrahydrofuranHCID 8028—
Produkt3-Chloro-9-bromo-8-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl methoxy)-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-oneHCID 6683432068,3%

Reaktionsbedingungen

Temperatur40 °C

Reaktionsschritte

Under nitrogen atmosphere, 9-bromo-3-chloro-8-hydroxy-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one (Compound S2-4, 112 mg, 0.29 mmol) and triphenylphosphine (227 mg, 3 eq.) were added with THF (2 ml), and ((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol (114 mg, 3 eq.) and 2.19 N toluene solution (0.4 mL, 3 eq.) of diethyl azodicarboxylic acid were added dropwise thereto, followed by stirring at 40° C. for 12 hr under nitrogen atmosphere. The residues obtained from the reaction solution after concentration under reduced pressure were purified by silica gel column chromatography (ethyl acetate/dichloromethane) to obtain the title compound (white powder, 100 mg).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS09440922B2
Quelldatensatzuspto-grants-2016_09
ORD IDord-6aad72284c7c4a32a5049efbfa4834e1
Quellennotizuspto-grants-2016_09