Potassium Carbonate → 2-Chloro-3'-fluoro-5-methoxy-1,1'-biphenyl

반응식

Br[C:2]1[CH:3]=[C:4]([O:9][CH3:10])[CH:5]=[CH:6][C:7]=1[Cl:8].[F:11][C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>>[Cl:8][C:7]1[CH:6]=[CH:5][C:4]([O:9][CH3:10])=[CH:3][C:2]=1[C:16]1[CH:15]=[CH:14][CH:13]=[C:12]([F:11])[CH:17]=1

참가 물질

반응물 3

HCID 11430Potassium Carbonate

HCID 27339863-Fluorophenylboronic acid

HCID 242120812-Bromo-1-chloro-4-methoxybenzene

생성물 1

HCID 866875982-Chloro-3'-fluoro-5-methoxy-1,1'-biphenyl

실험 절차

A round-bottom flask was charged with 3-bromo-4-chloroanisole (1.625 ml, 7.34 mmol), (3-fluorophenyl)boronic acid (1.129 g, 8.07 mmol), potassium carbonate (3.04 g, 22.01 mmol), and tetrakistriphenylphosphine palladium (0) (0.424 g, 0.367 mmol). The flask was flushed with Ar (g), then 1,4-dioxane (19.57 ml) and water (4.89 ml) were added. A reflux condenser was attached, and the flask was lowered into a 90° C. heating bath. After 2 h, the mixture was cooled, diluted with ethyl acetate, and washed with brine. The organic layer was dried over sodium sulfate, filtered, and concentrated. The residue was purified by chromatography on silica gel (80-g Redi-Sep Gold column, 0-10% EtOAc/Heptane) to give an oily solid as product that was used directly in the next step. m/z (ESI) 281.1 (M+H)+.