Hydrochloric Acid → HCID 53404021, compound

Participants

Reaction Conditions

Reaction Steps

Lithium bis(trimethylsilyl)amide (1M in tetrahydrofuran, 9.9 mL, 9.9 mmol) was added dropwise over 2 minutes to a cooled (10° C.) solution of 3-iodo-4-methylbenzonitrile (preparation 51a, 2.00 g, 8.2 mmol) in tetrahydrofuran (10 mL). After 1.5 hours, the mixture was cooled to 0° C. and water (20 mL) was slowly added. The pH was adjusted to 1 with 3M aqueous hydrochloric acid and then the mixture was stirred for 30 minutes. The aqueous layer was extracted with diethyl ether and ethyl acetate and then made basic with sodium hydroxide pellets which resulted in the separation of an oil. The mixture was extracted with ethyl acetate and the organic layer was dried and evaporated under reduced pressure. The residue was triturated with diethyl ether to give the title compound (0.54 g, 25%) as a yellow solid.

Provenance & Evidence