4-Cyanophenylacetic acid → 6-Chloro-2-(4-cyanophenyl)hexanoic acid

Participants

Reaction Steps

Step AU (1): 2-(4-Cyanophenyl)acetic acid (5.0 g, 31.0 mmol) was deprotonated with NaHMDS (2.0 M in THF, 46.5 mL, 93 mmol) and reacted with 1-chloro-4-iodobutane (10.2 g, 46.5 mmol) using a procedure analogous to Step AC (1) to afford, after purification by silica gel column chromatography, 6-chloro-2-(4-cyanophenyl)hexanoic acid (5.59 g, 22.2 mmol, 72% yield) as a white solid.

Provenance & Evidence