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

HRID 1803201Notes

Reaction equation

HRID 1803201 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1)#[N:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Cl:23][CH2:24][CH2:25][CH2:26][CH2:27]I>>[Cl:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:9]([C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=1)[C:10]([OH:12])=[O:11]

Participants

4

Reactant 3

HCID 795874-Cyanophenylacetic acidHCID 825271-Chloro-4-iodobutaneHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 581101896-Chloro-2-(4-cyanophenyl)hexanoic acidYield 72%

Procedure

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.

Workup

  1. customto afford

Sources & evidence

ORD record
ord-65fc4954b4a54ddc948146c480f855ae
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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