Benzoyl chloride, 3-chloro- → HCID 69195748, compound

Participants

Reaction Conditions

Reaction Steps

iso-Propyl magnesium chloride (2M solution in tetrahydrofuran) (2.85 ml, 5.7 mmol) was added dropwise over 5 mins to a stirred solution of 8-chloro-3-iodoquinoline (D1)(1.5 g, 5.2 mmol) in tetrahydrofuran (15 ml) at −40° C. under argon. After stirring the solution at this temperature for 0.3 h, copper (I) cyanide (0.47 g, 5.2 mmol) was added in portions over 5 mins. The whole mixture was left to stir at −40° C. for a further 10 mins and then 3-chlorobenzoyl chloride (1.0 g, 5.7 mmol) was added dropwise over 10 mins. The temperature was maintained at −40° C. for 0.5 h and then the reaction was warmed to 0° C. at which temperature it was quenched by the addition of a saturated solution of sodium chloride (100 ml). The mixture was extracted with ethyl acetate (2×50 ml). The combined extracts were dried (MgSO4) and concentrated in vacuo to a solid. The solid was purified by chromatography over silica gel eluting with a gradient of acetone/toluene to give the title compound (D5) as a white solid (0.95 g, 3.1 mmol, 60%).

Provenance & Evidence