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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 473492Generated: October 27, 2026

2-Bromo-5-fluoroanisole → 8-Nitro-3-(4-fluoro-2-methoxyphenylamino)-6H-dibenzo[b,e]oxepin-11-one

https://huagongshe.com/reaction/473492

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2-Bromo-5-fluoroanisoleHCID 7018043—
Reactant2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 11155794—
ReactantPotassium tert-butoxideHCID 23665647—
Reactant3-Amino-8-nitro-6H-dibenzo[b,e]oxepin-11-oneHCID 67361719—
Catalystpalladium(II) acetateHCID 167845—
SolventTolueneHCID 1140—
Solventtert-ButanolHCID 6386—
Product8-Nitro-3-(4-fluoro-2-methoxyphenylamino)-6H-dibenzo[b,e]oxepin-11-oneHCID 67360627—

Reaction Conditions

Temperature100 °C

Reaction Steps

In accordance with general method Z, 0.70 g (2.60 mmol) of (6), 0.55 g (2.68 mmol) of 2-bromo-5-fluoroanisole, 2 spatula tips of Pd(OAc)2, 0.10 g of 2-(dicyclohexylphosphino)-2′,4′,6′-triisopropylbiphenyl (phosphine ligand), 0.50 g of KOt-Bu, 2.0 ml of t-BuOH are weighed out and dissolved in 10 ml of toluene (anhydrous). The mixture is refluxed at 100° C. under an argon atmosphere for 4 h. The crude product is purified by chromatography over silica gel with MC/EtOH (98/2). Yield: 0.07 g (0.01%); melting point: 222.3° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08633312B2
Source datasetuspto-grants-2014_01
ORD IDord-5a3ff32a02374f7d9d6c0bacb5b0db6b
Source noteuspto-grants-2014_01