2-chloro-4-prop-2-enylbenzonitrile

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 4-Allyl-2-chlorobenzonitrile (265 mg, 1.5 mmol) in DCM (2 mL) and methanol (2 mL) was cooled to −78° C. Then O3 was bubbled into for 10 minutes. Then dimethylsulfide (1 mL) was added and the mixture was stirred at RT for 5 hours. The mixture was concentrated in vacuo to give the title product. Then O3 was bubbled into for 10 minutes Then dimethylsulfide (1 mL) was added The mixture was concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-bromo-2-chlorobenzonitrile (22 mg, 1.0 mmol), allyl tri-n-butylstannane (400 mg, 1.2 mmol), lithium chloride (126 mg, 3.0 mmol), and Pd(PPh3)4, (18 mg, 0.04 mmol) in toluene (10 mL), was refluxed overnight. Then the reaction was quenched with aq. KF (10 mL), extracted with ethyl acetate (10 mL×3), dried over Na2SO4, concentrated in vacuo. The residue was purified by chromatography to give the title product. was refluxed overnight Then the reaction was quenched with aq. KF (10 mL) extracted with ethyl acetate (10 mL×3) dried over Na2SO4 concentrated in vacuo The residue was purified by chromatography