Benzeneacetic acid, 2-fluoro- → 6-Chloro-2-(2-fluorophenyl)hexanoic acid

HRID 1803197Notes

Reaction equation

HRID 1803197 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Cl:22][CH2:23][CH2:24][CH2:25][CH2:26]I>>[Cl:22][CH2:23][CH2:24][CH2:25][CH2:26][CH:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])[C:9]([OH:11])=[O:10]

Participants

4

Reactant 3

HCID 67979Benzeneacetic acid, 2-fluoro-HCID 825271-Chloro-4-iodobutaneHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 581100566-Chloro-2-(2-fluorophenyl)hexanoic acidYield 89.6%

Procedure

Step AQ (1): 2-(2-Fluorophenyl)acetic acid (5 g, 32.4 mmol) was deprotonated with NaHMDS (2.0 M in THF, 32.4 mL, 64.9 mmol) and reacted with 1-chloro-4-iodobutane (3.97 mL, 32.4 mmol) using a procedure analogous to Step AC (1) to afford 6-chloro-2-(2-fluorophenyl)hexanoic acid (7.10 g, 89% yield). LC-MS (M−H)− 243.1. The crude product was used for subsequent chemistry without purification.

Sources & evidence

ORD record
ord-cf46e4e4bf9b47159115a74653c350ac
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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