HCID 19108688, compound → HCID 19108704, compound

HRID 327657Notes

Reaction equation

HRID 327657 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8]C)=[CH:4][C:3]=1[N:10]1[CH:14]=[CH:13][N:12]=[CH:11]1>Br>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N:10]1[CH:14]=[CH:13][N:12]=[CH:11]1

Participants

3

Reactant 1

HCID 19108688HCID 19108688, compound

Product 1

HCID 19108704HCID 19108704, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

1-chloro-2-(1H-imidazol-1-yl)-4-methoxybenzene (7.5 g, 0.036 m) was mixed with 40 ml 48% hydrobromic acid. The solution was distilled until the head temperature reached 120° C. and the reaction was then heated at reflux for two hours. The reaction was concentrated under reduced pressure. The residue was triturated in isopropyl alcohol-isopropyl ether and the solid was collected. The solid was dissolved in water and poured into a saturated solution of sodium bicarbonate. The solid was collected and rinsed with water, isopropyl alcohol-isopropyl ether, and isopropyl ether to give 6.65 g of solid. A small portion of this solid was recrystallized by dissolving in methanol-isopropyl alcohol, treated with charcoal, filtered, and evaporated to remove most of the methanol. A white solid was obtained which was dried at 70° C. under vacuum overnight, mp 204°-205° C.

Workup

  1. distillationThe solution was distilled until the head temperature
  2. customreached 120° C.
  3. temperaturethe reaction was then heated
  4. temperatureat reflux for two hours
  5. concentrationThe reaction was concentrated under reduced pressure
  6. customThe residue was triturated in isopropyl alcohol-isopropyl ether
  7. customthe solid was collected
  8. dissolutionThe solid was dissolved in water
  9. additionpoured into a saturated solution of sodium bicarbonate
  10. customThe solid was collected
  11. washrinsed with water, isopropyl alcohol-isopropyl ether, and isopropyl ether

Sources & evidence

ORD record
ord-7ba8e6593c5a4e2381dbf75533771bfb
Source dataset
uspto-grants-1993_12
Patent number
US05273993

Reaction notes

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