Bromide ion → 1-(2,4-Difluorophenyl)piperazine

Participants

Role	Name	HCID	Charge
Reactant	Bromide ion	HCID 259	—
Reactant	Piperazine	HCID 4837	—
Reactant	1-Bromo-2,4-difluorobenzene	HCID 67674	—
Reactant	Binap, (A+-)-	HCID 634876	—
Reactant	Sodium t-butoxide	HCID 23676156	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Toluene	HCID 1140	—
Product	1-(2,4-Difluorophenyl)piperazine	HCID 2734637	—

Reaction Conditions

Temperature	110 °C

Reaction Steps

1-(2,4-Difluorophenyl)piperazine is prepared from 2,4-difluorobromobenzene. To the bromide (8.0 g, 41.4 mmol), piperazine (21.4 g, 249 mmol), sodium t-butoxide (5.6 g, 58 mmol) and BINAP (1.55 g, 2.5 mmol) in toluene (20 ml), add Pd2(dba)3 (0.477 g, 0.83 mmol). Heat the mixture at 110° C. under N2 for 20 h. Allow to cool and extract with 1N HCl. Basify the extract with NaOH to pH=10, extract with CH2Cl2, dry and concentrate to obtain the title compound as a brown oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06630475B2
Source dataset	uspto-grants-2003_10
ORD ID	ord-2a7660205109476399f4f9a27766477d
Source note	uspto-grants-2003_10