1-Chloro-4-iodobutane → HCID 58110068, compound

HRID 1803193Notes

Reaction equation

HRID 1803193 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1.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:3]=[C:2]([F:1])[CH:7]=[C:6]([F:8])[CH:5]=1)[C:10]([OH:12])=[O:11]

Participants

4

Reactant 3

HCID 825271-Chloro-4-iodobutaneHCID 1454243,5-Difluorophenylacetic acidHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 58110068HCID 58110068, compoundYield 85.3%

Procedure

Step AL (1): 2-(3,5-Difluorophenyl)acetic acid (2.5 g, 14.5 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-(3,5-difluorophenyl)hexanoic acid (3.25 g, 85% yield). LC-MS (m-H)− 261.1. The crude product was used for subsequent chemistry without purification.

Sources & evidence

ORD record
ord-de40b7223dbb4c05bc44b88347af6af2
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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