4-Bromobenzaldehyde → HCID 59327794, compound

https://huagongshe.com/reaction/1193024

Participants

Role	Name	HCID	Charge
Reactant	4-Bromobenzaldehyde	HCID 70741	—
Reactant	Tris(1,1-dimethylethyl)phosphine	HCID 83681	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Reactant	N-Phenyl-4-(trimethylsilyl)aniline	HCID 44138892	—
Catalyst	(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium	HCID 6505921	—
Solvent	Toluene	HCID 1140	—
Product	HCID 59327794	HCID 59327794	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

4-(trimethylsilyl)-N-phenylbenzeneamine (22.8 m mol)), 4-bromobenzaldehyde (29.64 m mol)), tris(dibenzylideneaceton)dipalladium(O) (0.342 m mol)), tris-tert-butyl phosphine (0.684 m mol)), and sodium-tert-butoxide (29.64 m mol)) were dissolved in toluene (100 ml) in a 250 ml tri-neck-round bottom flask and were then stirred in a bath of 100° C. for 24 hours. After the reaction was terminated, the toluene was removed from the solution. After extraction was performed on the solution using dichloromethane and water, the resulting solution was reduced in pressure and distilled. After a silica gel column chromatography, the solvent was reduced in pressure and distilled, thereby obtaining 4-(N-(4-(trimethylsilyl)phenyl)-N-phenylamino)benzaldehyde liquid having 4.1 g.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08680336B2
Source dataset	uspto-grants-2014_03
ORD ID	ord-2cfb52ab518847418a8733955291ffe3
Source note	uspto-grants-2014_03