Potassium Carbonate → HCID 86724236, compound

HRID 873698Notes

Reaction equation

HRID 873698 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([I:9])[CH:3]=1.Br[CH2:11][C:12](=[O:17])[CH2:13][CH2:14][CH2:15][Cl:16].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:11][C:12](=[O:17])[CH2:13][CH2:14][CH2:15][Cl:16])=[C:4]([I:9])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 109245324-Bromo-2-iodophenolHCID 1225843959554-91-5

Product 1

HCID 86724236HCID 86724236, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The mixture of 4-bromo-2-iodophenol (3.30 g, 11.04 mmol), 1-bromo-5-chloropentan-2-one (75% purity, 3.9 g, 14.66 mmol), and K2CO3 (2.3 g, 16.64 mmol) in acetone (66 mL) was stirred for 48 hours at ambient temperature. The insoluble material was removed by filtration and washed with EtOAc. The filtrate was evaporated in vacuo. The residue was purified by silicagel column chromatography (EtOAc-hexane, a linear gradient of EtOAc from 0 to 25%) afforded 1-(4-bromo-2-iodophenoxy)-5-chloropentan-2-one (2.12 g).

Workup

  1. customThe insoluble material was removed by filtration
  2. washwashed with EtOAc
  3. customThe filtrate was evaporated in vacuo
  4. customThe residue was purified by silicagel column chromatography (EtOAc-hexane

Sources & evidence

ORD record
ord-417e74c2b2e140b6a12e64d2ac741053
Source dataset
uspto-grants-2015_03
Patent number
US08975415B2

Reaction notes

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