Iodoethane → HCID 22721046, compound

HRID 1582485Notes

Reaction equation

HRID 1582485 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[O:9][CH:10]([CH3:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+].[CH2:19](I)[CH3:20]>CC(C)=O.C(OCC)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:19][CH3:20])=[CH:4][C:3]=1[O:9][CH:10]([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 22720969HCID 22720969, compound

Product 1

HCID 22721046HCID 22721046, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 4-bromo-3-isopropoxy-phenol (0.50 g, 2.16 mmol) in acetone (3 mL) were added potassium carbonate (0.30 g, 2.16 mmol) and ethyl iodide (0.35 mL, 4.33 mmol). The reaction mixture was heated at gentle reflux for 12 h. The solvent was removed to give a white paste. It was then taken in diethyl ether (50 mL). The white solids were filtered off and the filtrate was concentrated. Purification of the residue by Biotage flash chromatography eluting with 10% ethyl acetate in hexanes gave 1-bromo-4-ethoxy-2-isopropoxy-benzene (0.48 g, 86%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat gentle reflux for 12 h
  3. customThe solvent was removed
  4. customto give a white paste
  5. filtrationThe white solids were filtered off
  6. concentrationthe filtrate was concentrated
  7. customPurification of the residue by Biotage flash chromatography
  8. washeluting with 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-db9a17c8031b43509301ec51deb35467
Source dataset
uspto-grants-2004_05
Patent number
US06734302B2

Reaction notes

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