2,9-Dimethyl-1,10-phenanthroline → HCID 69006936, compound

Participants

Reaction Conditions

Reaction Steps

A dry round bottomed flask was charged with NaOtBu (398 mg, 4.14 mmol), CuI (62 mg, 0.33 mmol), neocuproin (66 mg, 0.30 mmol), 3-fluoro-thiophenol (394 mg, 3.07 mmol) and 3-chloro-2-iodoanisole (698 mg, 2.60 mmol). The flask was evacuated and backfilled with Ar three times. Dry toluene (10 mL) was added and the mixture stirred at 105° C. overnight. The mixture was diluted with toluene (40 mL) and filtered through a pad of silica gel and evaporated to dryness to give a quantitative yield of crude 1-Chloro-2-(3-fluoro-phenylsulfanyl)-3-methoxy-benzene. The material was dissolved in toluene (20 mL) and cooled to 0° C. Neat BBr3 (0.38 mL, 4.02 mmol) was added dropwise and the mixture was allowed to reach room temperature overnight. The mixture was quenched by the addition of H2O/ice (80 mL) and diethyl ether (100 mL). The organic layer was washed with brine. After drying over Na2SO4 the crude product was adsorbed onto silica gel. After flash chromatography using silica gel, eluting with heptanes/EtOAc, 96:4 the title compound was obtained as a yellow oil Yield: 642 mg, 97% over two steps.

Provenance & Evidence