Potassium Carbonate → 4-Bromo-3-propoxy-phenol

HRID 1167294

Reaction equation

HRID 1167294 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][C:3]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].I[CH2:17][CH2:18][CH3:19]>CC(C)=O>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][C:3]=1[O:9][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 811054-Bromoresorcinol

Product 1

HCID 229961784-Bromo-3-propoxy-phenolYield 57%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-bromoresorcinol (1 g, 5.291 mmol) in acetone (10 mL) were added potassium carbonate (732 mg, 5.291 mmol) and 1-iodopropane (1.799 g, 10.58 mmol), respectively. The reaction mixture was heated at gentle reflux for 6 h. The solvent was removed and the residue was taken in diethyl ether (50 mL). The white solid was filtered off, and the filtrated was concentrated in vacuo. Purification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 10% ethyl acetate in hexanes yielded 4-bromo-3-propoxy-phenol as a white solid (693 mg, 57%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat gentle reflux for 6 h
  3. customThe solvent was removed
  4. filtrationThe white solid was filtered off
  5. concentrationthe filtrated was concentrated in vacuo
  6. customPurification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel)
  7. washeluting with 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-f66b0d1818bd4510b0b0ada6703b2fd3
Source dataset
uspto-grants-2003_09
Patent number
US06617346B1

Linked notes

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