3-Fluorophenylacetic acid → HCID 58110117, compound

HRID 1803195Notes

Reaction equation

HRID 1803195 reaction equation
[F: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]([F:1])[CH:3]=1)[C:9]([OH:11])=[O:10]

Participants

4

Reactant 3

HCID 676173-Fluorophenylacetic acidHCID 825271-Chloro-4-iodobutaneHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 58110117HCID 58110117, compoundYield 91.6%

Procedure

Step AO (1): 2-(3-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-(3-fluorophenyl)hexanoic acid (7.26 g, 91% yield). LC-MS (M−H)− 243.2. The crude product was used for subsequent chemistry without purification.

Sources & evidence

ORD record
ord-9335ff44d4e64c678b3d62778b6f8a11
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

Loading…