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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 75074Generated: October 25, 2026

1-Bromo-2-fluorobenzene → 2,4-diphenyl-N-2-fluorophenylbenzenamine

https://huagongshe.com/reaction/75074

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1-Bromo-2-fluorobenzeneHCID 61259—
ReactantSodiumHCID 5360545—
Reactant2,4-DiphenylanilineHCID 12316638—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventTolueneHCID 1140—
Product2,4-diphenyl-N-2-fluorophenylbenzenamineHCID 5935759261.9%

Reaction Conditions

Temperature100 °C

Reaction Steps

2,4-diphenylaniline (12 mmol), 1-bromo-2-fluorobenzene (10 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.15 mmol), (±)-2,2′-bis(diphenylphosphine)-1,1′-binaphthalene (0.3 mmol) and sodium tert-butoxie (14 mmol) are put in a two-neck round-bottom flask and dissolved in toluene (30 mL). Subsequently, the resulting solution is stirred in a bath under a temperature of about 100° C. for 24 hours. After completion of the reaction, toluene is removed. The reaction mixture is extracted with dichloromethane and water, and then being distilled under reduced pressure. The resulting residence is filtered by silica gel column and distilled under reduced pressure again. Next, by re-crystallizing and filtering with dichloromethane and petroleum ether, 2,4-diphenyl-N-2-fluorophenylbenzenamine (2.1 g) is yielded.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08835020B2
Source datasetuspto-grants-2014_09
ORD IDord-bc715d726b214670b8b515c9efd95368
Source noteuspto-grants-2014_09