Potassium Phosphate, Tribasic → Methyl 2'-formyl-3'-methoxy-5'-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	4-Methoxycarbonylphenylboronic acid	HCID 2734369	—
Reactant	2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl	HCID 11269872	—
Reactant	2-Chloro-6-methoxy-4-(trifluoromethyl)benzaldehyde	HCID 84070292	—
Catalyst	Palladium (II) acetate	HCID 4144353	—
Solvent	Water	HCID 962	—
Solvent	Toluene	HCID 1140	—
Product	Methyl 2'-formyl-3'-methoxy-5'-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxylate	HCID 86674212	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

2-Chloro-6-methoxy-4-(trifluoromethyl)benzaldehyde (224 mg, 0.94 mmol), (4-(methoxycarbonyl)phenyl)boronic acid (219 mg, 1.22 mmol), S-PHOS (115 mg, 0.28 mmol), Pd(Oac)2 (32 mg, 0.14 mmol) and K3PO4 (597 mg, 2.81 mmol) were dissolved in wet PhMe (8 mL) and the resulting mixture was heated to 80° C. After 16 h the resulting mixture was diluted with water and extracted with EtOAc. The combined organic extracts were dried (Na2SO4), concentrated, and purified via column chromatography to yield the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09045389B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-021c7943dc3246688865febbcf8e9216
Source note	uspto-grants-2015_06