Potassium Carbonate → 2,2,2-Trifluoro-1-[2-(3-phenyl-pyrazol-1-yl)-phenyl]-ethanol

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	trans-N,N'-dimethyl-1,2-cyclohexanediamine	HCID 2733821	—
Reactant	2-Iodo-alpha-(trifluoromethyl)benzyl Alcohol	HCID 66743698	—
Reactant	HCID 178420101	HCID 178420101	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Toluene	HCID 1140	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	2,2,2-Trifluoro-1-[2-(3-phenyl-pyrazol-1-yl)-phenyl]-ethanol	HCID 66743644	23.6%

Reaction Conditions

Temperature	130 °C

Reaction Steps

2,2,2-Trifluoro-1-(2-iodo-phenyl)-ethanol (0.331 g, 1.1 mmol), 3-phenyl pyrazole (0.144 g, 1.0 mmol), CuI (0.019 g, 0.1 mmol), K2CO3 (0.290 g, 2.1 mmol), (1R,2R)-N,N′-dimethyl-cyclohexane-1,2-diamine (0.028 g, 0.2 mmol) and toluene (10 ml) were taken in a 20 ml pressure tube and the mixture was heated at 130° C. (oil bath temperature) for 12 h. The mixture was diluted with ethyl acetate and washed with H2O (2×20 ml), brine, and dried over sodium sulfate. Removal of solvent gave a crude product, which was purified by ISCO column chromatography using 5-10% ethyl acetate in hexane as solvent to afford 2,2,2-trifluoro-1-[2-(3-phenyl-pyrazol-1-yl)-phenyl]-ethanol (75 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07709493B2
Source dataset	uspto-grants-2010_05
ORD ID	ord-835fc95833c2480d8a9d7c9e1cf7f183
Source note	uspto-grants-2010_05