1-Chloro-4-iodobutane → 6-Chloro-2-(2,4-dichlorophenyl)hexanoic acid

HRID 1803188Notes

Reaction equation

HRID 1803188 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([OH:12])=[O:11].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:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1])[C:10]([OH:12])=[O:11]

Participants

4

Reactant 3

HCID 825271-Chloro-4-iodobutaneHCID 882092,4-Dichlorophenylacetic acidHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 581101626-Chloro-2-(2,4-dichlorophenyl)hexanoic acidYield 60.2%

Procedure

Step AF (1): 2-(2,4-Dichlorophenyl)acetic acid (2.5 g, 12.19 mmol) was deprotonated with NaHMDS (1.0 M in THF, 24.0 mL, 24.4 mmol) and reacted with 1-chloro-4-iodobutane (1.49 mL, 12.2 mmol) using a procedure analogous to Step AC (1) to afford, after purification by silica gel column chromatography, 6-chloro-2-(2,4-dichlorophenyl)hexanoic acid (2.17 g, 7.34 mmol, 60% yield) as a colorless oil. LC-MS (M−H)− 295.1.

Workup

  1. customto afford

Sources & evidence

ORD record
ord-0585e07e50bb4a2ab2720b99f851a0e0
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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