Water → 4-Hydroxy-(1,1'-biphenyl)-3-carbaldehyde

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Dichloromethane	HCID 6344	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	Phenylboronic Acid	HCID 66827	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water 1,2-dimethoxyethane	HCID 18180031	—
Product	4-Hydroxy-(1,1'-biphenyl)-3-carbaldehyde	HCID 12264658	50%

Reaction Conditions

Temperature	100 °C

Reaction Steps

(Fahmy, A. M.; Revue Roumaine de Chimie 1985, V30(8), P749-52) Bromosalicaldehyde (S1, 525 mg, 2.6 mmol), phenylboronic acid (S2, 349 mg, 2.86 mmol), Pd(dppf)Cl2.CH2Cl2 (106 mg, 0.13 mmol) and Na2CO3 (413 mg, 3.9 mmol) were dissolved in degassed DME/H2O (3:1) and stirred at reflux (100° C.) for 5 h. After cooling, the mixture was poured into water and extracted with DCM (3×100 ml). The combined organic layers were dried over Na2SO4 and the residue purified by silica gel chromatography (Et2O, 100%) to afford the title compound (250 mg, 50%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08563557B2
Source dataset	uspto-grants-2013_10
ORD ID	ord-e81718c76b784abb83d3e438479e8b3f
Source note	uspto-grants-2013_10