Sodium Carbonate → 2',4'-Difluoro-3-hydroxy[1,1'-biphenyl]-4-carbaldehyde

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	2,4-Difluorophenylboronic acid	HCID 2734334	—
Reactant	4-Bromo-2-hydroxybenzaldehyde	HCID 4066019	—
Reactant	2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl	HCID 11269872	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Solvent	Water	HCID 962	—
Solvent	Toluene	HCID 1140	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	2',4'-Difluoro-3-hydroxy[1,1'-biphenyl]-4-carbaldehyde	HCID 53220373	97.3%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of 4-bromo-2-hydroxybenzaldehyde (7.5 g), (2,4-difluorophenyl)boronic acid (8.84 g), tris(dibenzylideneacetone)dipalladium (0) (1.367 g), 2M aqueous sodium carbonate solution (56.0 mL) and dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (1.53 g) in toluene (70 mL) was stirred at 100° C. under nitrogen atmosphere overnight. The mixture was diluted with ethyl acetate and water. The organic layer was separated and concentrated in vacuo. The residue was passed through a silica gel pad and concentrated in vacuo. The residue was crystallized from methanol-water (80 mL-20 mL) to give the title compound (8.50 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09353108B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-298f52b8b3634dd3988285784454a942
Source note	uspto-grants-2016_05