Water → 4′-(Dimethylamino)-4-hydroxy[1,1′-biphenyl]-3-carboxaldehyde

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	5-Bromosalicylaldehyde	HCID 72863	—
Reactant	4-(Dimethylamino)phenylboronic acid	HCID 2734344	—
Catalyst	Ferrocene-1,1'-bis-(diphenylphosphine)	HCID 635956	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	4′-(Dimethylamino)-4-hydroxy[1,1′-biphenyl]-3-carboxaldehyde	HCID 59784648	64%

Reaction Conditions

Temperature	100 °C

Reaction Steps

Within a vacuum tube, 5-bromo-2-hydroxybenzaldehyde (0.5 g, 2.49 mmol), 4-dimethylaminophenyl boronic acid (0.62 g, 3.73 mg), dichloro[1,1′-ferrocenylbis(diphenyl-phosphine)]palladium(II)dichloromethane (Pd(dppf)Cl2, 0.33 g, 0.40 mmol, ‘dppf’=1,1′-bis(diphenylphospino)ferrocene) and sodium carbonate (0.53 g, 4.98 mmol) were dissolved in ethylene glycol dimethylether:water (15 ml:5 ml), followed by stirring at 100° C. for 4 hours. The reaction product thus obtained was diluted in ethyl acetate, washed with brine, dried over anhydrous MgSO4, and concentrated. The concentrate was purified through column chromatography (10% ethyl acetate/hexane) and the fraction was concentrated to give 4′-dimethylamino-4-hydroxybiphenyl-3-carbaldehyde (0.383 g, 64%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08148541B2
Source dataset	uspto-grants-2012_04
ORD ID	ord-089e59e52a95447eba4bfa0a929b2741
Source note	uspto-grants-2012_04