1-Chloro-3-iodopropane → 2,4-Dichloro-α-(3-chloropropyl)benzeneacetic acid

HRID 1803186Notes

Reaction equation

HRID 1803186 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]I>>[Cl:23][CH2:24][CH2:25][CH2:26][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 813631-Chloro-3-iodopropaneHCID 882092,4-Dichlorophenylacetic acidHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 581100252,4-Dichloro-α-(3-chloropropyl)benzeneacetic acidYield 58%

Procedure

Step AD (1): 2-(2,4-Dichlorophenyl)acetic acid (10.25 g, 50.0 mmol) was deprotonated with NaHMDS (1.0 M in THF, 100 mL, 100 mmol) and reacted with 1-chloro-3-iodopropane (5.27 mL, 50.0 mmol) using a procedure analogous to Step AC (1) to afford, after purification by silica gel column chromatography, 5-chloro-2-(2,4-dichlorophenyl)pentanoic acid (8.15 g, 28.9 mmol, 58% yield) as a colorless oil. MS (M+H)+ 280.9. 1H NMR (500 MHz, chloroform-d) δ ppm 7.47 (d, J=2.14 Hz, 1 H) 7.34-7.40 (m, 1 H) 7.28-7.33 (m, 1 H) 4.22 (t, J=7.48 Hz, 1 H) 3.57 (t, J=6.41 Hz, 2 H) 2.27 (dddd, J=13.08, 10.64, 7.55, 5.34 Hz, 1 H) 1.95-2.05 (m, 1 H) 1.82-1.92 (m, 1 H) 1.68-1.81 (m, 1 H).

Workup

  1. customto afford

Sources & evidence

ORD record
ord-186ed9c412f14a7a996c348dcf88b55c
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

Loading…