Potassium Iodide → 4-(4-Bromo-butoxy)-3-fluoro-benzoic Acid Ethyl Ester

HRID 220910Notes

Reaction equation

HRID 220910 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5]Br.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH2:15]([O:17][C:18](=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([F:26])[CH:20]=1)[CH3:16]>CC(C)=O>[CH2:15]([O:17][C:18](=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:5][CH2:4][CH2:3][CH2:2][Br:1])=[C:21]([F:26])[CH:20]=1)[CH3:16]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 13745619Ethyl 3-fluoro-4-hydroxybenzoate

Product 1

HCID 575552954-(4-Bromo-butoxy)-3-fluoro-benzoic Acid Ethyl EsterYield 80%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1,4-Dibromobutane (2.34 g, 10.8 mmol), potassium carbon-ate (1.86 g, 13.5 mmol) and potassium iodide (90 mg, 0.5 mmol) were added to a solution of 3-fluoro-4-hydroxy-benzoic acid ethyl ester from Example E27 (11.0 g, 5.4 mmol) in acetone (25 ml) and the mixture was heated at reflux for 20 h. The solid was filtered off, washed with EtOAc and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 15% EtOAc:85% hexane) to yield the title compound (1.38 g, 80%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 20 h
  3. filtrationThe solid was filtered off
  4. washwashed with EtOAc
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel (eluant; 15% EtOAc:85% hexane)

Sources & evidence

ORD record
ord-090972bc6b084d419a5bc596c5737e56
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

Loading…