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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 473490Generated: October 27, 2026

2-Bromoanisole → 3-(2-Methoxyphenylamino)-8-nitro-6H-dibenzo[b,e]oxepin-11-one

https://huagongshe.com/reaction/473490

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2-BromoanisoleHCID 11358—
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—
Product3-(2-Methoxyphenylamino)-8-nitro-6H-dibenzo[b,e]oxepin-11-oneHCID 67362958—

Reaction Conditions

Temperature100 °C

Reaction Steps

In accordance with general method Z, 0.80 g (2.96 mmol) of (6), 0.70 g (3.80 mmol) of 2-bromoanisole, 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: 0.025 g (2.2%); melting point: 200.3° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08633312B2
Source datasetuspto-grants-2014_01
ORD IDord-2e445cb7878145b2a0aab0981739d2f8
Source noteuspto-grants-2014_01