Water → 2',4,6'-Trifluorobiphenyl-3-carbaldehyde

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	1-Bromo-2,6-difluorobenzene	HCID 123557	—
Reactant	(4-Fluoro-3-formylphenyl)boronic acid	HCID 2778651	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Toluene	HCID 1140	—
Product	2',4,6'-Trifluorobiphenyl-3-carbaldehyde	HCID 64038831	49.4%

Reaction Conditions

Temperature	100 °C

Reaction Steps

To a solution of 2-bromo-1,3-difluorobenzene (100 g, 477.46 mmol) and 4-fluoro-3-formylphenylboronic acid (96.2 g, 572.95 mmol) in toluene (1432 mL) at RT was added Na2CO3 (2M in H2O) (477.46 mL, 954.2 mmol) and PdCl2(dppf) (7.798 g, 9.54 mmol). The reaction mixture was stirred at 100° C. for 8 h and cooled to RT. Water was added to the reaction mixture and extracted with EtOAc (2×500 mL). Organic layer was washed with brine and dried over Na2SO4. The organic layer was concentrated and purified by column using silica (100-200 mesh) and 0-5% EtOAc-hexane to provide 2′,4,6′-trifluorobiphenyl-3-carbaldehyde (54.3 g, 49.4% yield).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09090593B2
Source dataset	uspto-grants-2015_07
ORD ID	ord-61e63afbe4194cf69cdf0b326bef5c55
Source note	uspto-grants-2015_07