3-Chlorobenzaldehyde → HCID 69197213, compound

Participants

Reaction Steps

iso-Propyl magnesium chloride (2M solution in tetrahydrofuran)(3.76 ml, 7.5 mmol) was added dropwise over 0.25 h to a stirred solution of 8-chloro-3-iodoquinoline (D1)(2.0 g, 6.9 mmol) in tetrahydrofuran (16 ml) at −40° C. under argon. After stirring the solution at this temperature for 0.5 h, 3-chlorobenzaldehyde (0.77 ml, 6.8 mmol) was added dropwise over 10 mins. The solution was allowed to warm to ambient temperature over 1 h and then quenched by the addition of a saturated solution of sodium chloride (100 ml). The mixture was extracted with ethyl acetate (2×100 ml). The combined extracts were dried (MgSO4) and concentrated in vacuo to give the title compound (D2) as a crude solid (1.84 g, 6.0 mmol, 88%) which was used directly in the next stage (see D3).

Provenance & Evidence