Ethanol → 2,2,2-Trifluoro-1-(3'-methylbiphenyl-2-yl)ethanol

https://huagongshe.com/reaction/419262

Participants

Role	Name	HCID	Charge
Reactant	Ethanol	HCID 702	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	3-Tolylboronic acid	HCID 2733950	—
Reactant	1-(4-Bromophenyl)-2,2,2-trifluoroethanol	HCID 11219024	—
Catalyst	Palladium	HCID 23938	—
Solvent	Water	HCID 962	—
Solvent	Dichloromethane	HCID 6344	—
Product	2,2,2-Trifluoro-1-(3'-methylbiphenyl-2-yl)ethanol	HCID 66649251	72%

Reaction Conditions

Temperature	80 °C

Reaction Steps

1-(4-Bromophenyl)-2,2,2-trifluoroethanol (0.13 g, 0.525 mmol), m-tolylboronic acid (0.1 g, 0.736 mmol), Fibercat (4.28% Pd, 47 mgs, 0.0157 mmol Pd), K2CO3 (0.22 g, 1.576 mmol), EtOH (3 mls), and H2O (0.5 mls) were combined and heated at 80° C. for 4 hours. The reaction was shown complete by TLC (CH2Cl2). The mixture was cooled, filtered, concentrated, slurried in CH2Cl2, and chromatographed over silica gel (CH2Cl2) to give 0.1 g of 2,2,2-trifluoro-1-(3′-methylbiphenyl-2-yl)ethanol. Yield: 72%.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08093291B2
Source dataset	uspto-grants-2012_01
ORD ID	ord-584104220f0d4764b636c041037a4dd4
Source note	uspto-grants-2012_01