(3,4-Difluorophenyl)acetic acid → 6-Chloro-2-(3,4-difluorophenyl)hexanoic acid

HRID 1803189Notes

Reaction equation

HRID 1803189 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[F:8].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:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=1)[C:10]([OH:12])=[O:11]

Participants

4

Reactant 3

HCID 69571(3,4-Difluorophenyl)acetic acidHCID 825271-Chloro-4-iodobutaneHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 581100576-Chloro-2-(3,4-difluorophenyl)hexanoic acidYield 88%

Procedure

Step AG (1): 2-(3,4-Difluorophenyl)acetic acid (2.5 g, 14.52 mmol) was deprotonated with NaHMDS (1.0 M in THF, 29.0 mL, 29.0 mmol) and reacted with 1-chloro-4-iodobutane (1.78 mL, 14.5 mmol) using a procedure analogous to Step AC (1) to afford 6-chloro-2-(3,4-difluorophenyl)hexanoic acid (3.35 g, 88% yield). LC-MS (M−H)− 261.1.

Sources & evidence

ORD record
ord-b84876602eed46f2b6307f003d748f88
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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