Bromocyclopentane → 2-[4-(Cyclopentylthio)-2-fluoro-phenyl]propionic acid

HRID 1506867Notes

Reaction equation

HRID 1506867 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([SH:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH3:14])[C:10]([O:12]C)=[O:11].Br[CH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:16]1([S:8][C:6]2[CH:5]=[CH:4][C:3]([CH:9]([CH3:14])[C:10]([OH:12])=[O:11])=[C:2]([F:1])[CH:7]=2)[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 60155350Methyl 2-(2-fluoro-4-mercaptophenyl)propionate

Product 1

HCID 601553562-[4-(Cyclopentylthio)-2-fluoro-phenyl]propionic acidYield 95.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of compound (9) (0.53 g, 2.5 mmol), bromocyclopentane (0.32 mL, 3.0 mmol), and potassium carbonate (1.2 g, 8.8 mmol) in dry DMF (5 mL) was treated in the same manner as in Example 7. The obtained residue was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (4:1) solution followed by conventional hydrolysis to give 0.64 g (90%) of compound (17) of interest as white solid.

Workup

  1. washThe obtained residue was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (4:1) solution
  2. customfollowed by conventional hydrolysis

Sources & evidence

ORD record
ord-47c1a9faf29c49aab891673fa3c432ca
Source dataset
uspto-grants-2015_12
Patent number
US09221786B2

Reaction notes

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