2-(4-FLUOROPHENYL)QUINOLINE synthesis
- Product Name:2-(4-FLUOROPHENYL)QUINOLINE
- CAS Number:323-91-1
- Molecular formula:C15H10FN
- Molecular Weight:223.24
Yield:323-91-1 83%
Reaction Conditions:
with ammonium hydroxide;1,10-Phenanthroline;Cs2CO3 in N,N-dimethyl-formamide at 80; for 20 h;Sealed tube;
Steps:
Synthetic procedures and spectroscopic data
Typical procedure for the preparation of 4a: To a solution of 2-bromobenzaldehyde (1a, 0.5 mmol)and acetophenone (2a, 0.6 mmol) in DMF (3 mL) were added Cs2CO3 (1 mmol), CuI (0.05 mmol),1,10-phen (0.1 mmol) and 26% aqueous ammonia (3, 0.5 mL). Then the tube was sealed and the mixturewas stirred at 80 C under air atmosphere for 20 h. After being cooled to room temperature, it wasquenched with aqueous NH4Cl solution and extracted with ethyl acetate. The combined organic layerswere washed with H2O and brine, and then dried over anhydrous Na2SO4. The solvent was evaporatedunder vacuum and the crude product was purified by column chromatography eluting with petroleumether/ethyl acetate (50:1) to give 2-phenylquinoline (4a). Quinolines 4b-4q were obtained in a similar manner.
References:
Li, Bin;Guo, Chenhao;Fan, Xuesen;Zhang, Ju;Zhang, Xinying [Tetrahedron Letters,2014,vol. 55,# 43,p. 5944 - 5948] Location in patent:supporting information
