2,6-Dichlorobenzaldehyde → HCID 18332487, compound

Participants

Reaction Steps

A solution of methyl 4-(bromomethyl)benzoate (2.0 g, 8.7 mmol) in THF (4.4 ml) was added slowly to cut zinc foil (683 mg, 10.44 mmol) which had been activated with 1,2-dibromoethane (80 mg). After 3 h of stirring at room temperature 2 ml of the solution was referred to a solution of copper cyanide (396 mg, 4.4 mmol) and lithium chloride (356 mg, 8.4 mmol) in THF (4 ml) cooled to −78°. This solution was warmed to −20° and then cooled back to −78°. Boron trifluoride etherate (983 μl, 8 mmol) was then added followed by 2,6-dichlorobenzaldehyde (0.56 g, 3.2 mmol) in THF (1 ml). The reaction was stirred for 2 h and then allowed to warm slowly to room temperature. Water (20 ml) was then added and the reaction mixture extracted into EtOAc (3×25 ml) and the combined organics dried (Na2SO4) and evaporated. Purification by column chromatography (SiO2; hexane:EtOAc. 4:1) gave the title compound as a colourless oil (863 mg, 83%). δH (CDCl3) 7.95 (2H, m, ArH), 7.93-7.26 (4H, m, ArH), 7.17-7.12 (1H, m, ArH), 5.73-5.65 (1H, m, CH), 3.91 (3H, s, CO2Me), 3.43 (1H, dd, J 13.5, 8.4 Hz, CHAB4}L ) and 3.28 (1H, dd, J 13.5, 6.3Hz, CHAHB), m/z (ESI, 60V) 325(MH+).

Provenance & Evidence