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Potassium Iodide → 4-(3-Bromo-propoxy)-3-fluorobenzoic acid ethyl ester

HRID 220868
Notes
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Reaction equation

HRID 220868 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4]Br.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH2:14]([O:16][C:17](=[O:26])[C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([F:25])[CH:19]=1)[CH3:15]>CC(C)=O>[CH2:14]([O:16][C:17](=[O:26])[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:4][CH2:3][CH2:2][Br:1])=[C:20]([F:25])[CH:19]=1)[CH3:15]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 13745619Ethyl 3-fluoro-4-hydroxybenzoate

Product 1

HCID 575553074-(3-Bromo-propoxy)-3-fluorobenzoic acid ethyl esterYield 71%

Reagents, catalysts & solvents 1

HCID 180
Acetone
Solvent

Procedure

1,3-Dibromopropane (2.2 g, 11.0 mmol), potassium carbon-ate (1.86 g, 13.6 mmol) and potassium iodide (90 mg, 0.5 mmol) were added to 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 and washed with EtOAc. The filtrate was concentrated in vacuo and azeotroped with toluene. The residue was purified by flash chromatography on silica gel (eluant; 20% EtOAc:80% hexane) to yield the title compound (1.18 g, 71%).

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. customazeotroped with toluene
  7. customThe residue was purified by flash chromatography on silica gel (eluant; 20% EtOAc:80% hexane)

Sources & evidence

ORD record
ord-a829fcad336b485abe87ea058af5c1cb
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08202858B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes