o-Chlorophenylacetic acid → HCID 58110017, compound

HRID 1803198Notes

Reaction equation

HRID 1803198 reaction equation
[Cl: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[Cl:1])[C:9]([OH:11])=[O:10]

Participants

4

Reactant 3

HCID 17124o-Chlorophenylacetic acidHCID 825271-Chloro-4-iodobutaneHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 58110017HCID 58110017, compoundYield 97.6%

Procedure

Step AR (1): 2-(2-Chlorophenyl)acetic acid (5.0 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 (5.38 mL, 44.0 mmol) using a procedure analogous to Step AC (1) to afford 6-chloro-2-(2-chlorophenyl)hexanoic acid (7.47 g, 88% yield). LC-MS (M−H)− 259.1. The crude product was used for subsequent chemistry without purification.

Sources & evidence

ORD record
ord-44d72418e3f742879ff8daddfc515a1b
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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