1-Chloro-3-iodopropane → 5-Chloro-2-(4-(trifluoromethoxy)phenyl)pentanoic acid

HRID 1803226Notes

Reaction equation

HRID 1803226 reaction equation
[F:1][C:2]([F:15])([F:14])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=[O:12])=[CH:6][CH:5]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Cl:26][CH2:27][CH2:28][CH2:29]I>CCOC(C)=O.CCCCCC>[Cl:26][CH2:27][CH2:28][CH2:29][CH:10]([C:7]1[CH:6]=[CH:5][C:4]([O:3][C:2]([F:14])([F:15])[F:1])=[CH:9][CH:8]=1)[C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 813631-Chloro-3-iodopropaneHCID 2724254Sodium bis(trimethylsilyl)amideHCID 27773192-[4-(Trifluoromethoxy)phenyl]acetic acid

Product 1

HCID 581100785-Chloro-2-(4-(trifluoromethoxy)phenyl)pentanoic acidYield 10.1%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Step AAK (1): 2-(4-(Trifluoromethoxy)phenyl)acetic acid (3.54 g, 16.1 mmol) was deprotonated with NaHMDS (2.0 M in THF, 18.1 mL, 36.2 mmol) and reacted with 1-chloro-3-iodopropane (3.62 g, 17.7 mmol) using a procedure analogous to Step AC (1) to afford after purification by silica gel column chromatography (25-50% EtOAc/hexane), 5-chloro-2-(4-(trifluoromethoxy)phenyl)pentanoic acid (0.48 g, 1.62 mmol, 10% yield) as a pale-yellow oil. LC-MS (M−H)− 295.2.

Workup

  1. customto afford

Sources & evidence

ORD record
ord-7531fbdbff964c77a79392d72c9c282e
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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