Allyl iodide → 2-(3,4-Dichlorophenyl)pent-4-enenitrile

Participants

Reaction Conditions

Reaction Steps

3,4-Dichlorophenylacetonitrile (5 g, 26.87 mmol, 1 eq) in THF (50 mL) was cooled to −78° C. under Ar. LDA (2 M in THF, 16.1 mL, 32.2 mmol, 1.2 eq) was added and the reaction was warmed to 0° C. over 1 h. The reaction was re-cooled to −78° C. and allyl iodide (2.67 mL, 26.87 mmol, 1 eq) was added then the reaction was stirred at −78° C. for a further 2 h. The reaction was diluted with EtOAc (150 mL) and washed with aqueous HCl (1 M, 100 mL), saturated aqueous Na2S2O3 (100 mL) and saturated aqueous NaCl (100 mL). The organic extracts were dried over Na2SO4, filtered and concentrated by rotary evaporation to afford 2-(3,4-dichlorophenyl)-pent-4-ene-nitrile (6.3 g, ˜28 mmol) as a yellow oil.

Provenance & Evidence