3-Chlorophenylacetic acid → 6-Chloro-2-(3-chlorophenyl)hexanoic acid

HRID 1803196Notes

Reaction equation

HRID 1803196 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.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:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[C:9]([OH:11])=[O:10]

Participants

4

Reactant 3

HCID 158793-Chlorophenylacetic acidHCID 825271-Chloro-4-iodobutaneHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 581100916-Chloro-2-(3-chlorophenyl)hexanoic acidYield 98%

Procedure

Step AP (1): 2-(3-Chlorophenyl)acetic acid (5 g, 29.3 mmol) was deprotonated with NaHMDS (2.0 M in THF, 29.3 mL, 58.6 mmol) and reacted with 1-chloro-4-iodobutane (3.59 mL, 29.3 mmol) using a procedure analogous to Step AC (1) to afford 6-chloro-2-(3-chlorophenyl)hexanoic acid (7.47 g, 98% yield). LC-MS (M−H)− 259.1. The crude product was used for subsequent chemistry without purification.

Sources & evidence

ORD record
ord-95f5f8dda9e94b73b16e3fcfab6eac1d
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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