Potassium Carbonate → HCID 22633322, compound

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	5-Bromo-4-formyl-2-methoxyphenyl acetate	HCID 262348	—
Reactant	4-Isopropylphenylboronic acid	HCID 2773480	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 22633322	HCID 22633322	72%

Reaction Conditions

Temperature	80 °C

Reaction Steps

To a mixture of (273 mg, 1 mmol) of 4-Acetoxy-2-bromo-5-methoxybenzaldehyde, (164 mg, 1 mmol) of 4-isopropylphenylboronic acid and 276 mg (2 mmol) of K2CO3 in 5 mL of DMF and 1 mL of H2O was added 73.1 mg (0.1 mmol) of Pd(dppf)Cl2. The mixture was heated at 80° C. overnight. After the removal of the catalyst via filtration, the mixture was repartitioned between EtOAc and H2O. Aqueous layer was extracted 3 times with EtOAc and organic layers were combined and dried over Na2SO4. After the removal of the solvent, the residue was chromatographed to give 362 mg of 5-Hydroxy-4′-isopropyl-4-methoxy-biphenyl-2-carbaldehyde (72%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06825208B2
Source dataset	uspto-grants-2004_11
ORD ID	ord-9b402a2cfb4446f29d5c24932703bd13
Source note	uspto-grants-2004_11