Water → HCID 18791037, compound

HRID 1005289Notes

Reaction equation

HRID 1005289 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[CH:8]=[CH2:9].[Br:11][C:12]1[C:13]([F:20])=[CH:14][C:15]([Cl:19])=[C:16]([OH:18])[CH:17]=1.O>CN(C)C=O>[CH2:9]([O:18][C:16]1[CH:17]=[C:12]([Br:11])[C:13]([F:20])=[CH:14][C:15]=1[Cl:19])[CH:8]=[CH2:7]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 114474605-BROMO-2-CHLORO-4-FLUOROPHENOL

Product 1

HCID 18791037HCID 18791037, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

96.5 g (0.7 mol) of potassium carbonate and 54.9 g (0.45 mol) of allylbromide were added to a solution of 78.7 g (0.35 mol) of 5-bromo-2-chloro-4-fluorophenol in 350 ml of dimethylformamide. The reaction mixture was subsequently stirred for 1 hour and stirred into 2.5 l of water. The mixture was then extracted with dichloromethane (three times). The combined organic phases were washed with water (three times) and saturated aqueous sodium chloride solution (once), dried over magnesium sulfate and finally concentrated. The crude product was purified by distillation. Bp.: 106° C. (0.8 mbar); Yield: 85 g.

Workup

  1. extractionThe mixture was then extracted with dichloromethane (three times)
  2. washThe combined organic phases were washed with water (three times) and saturated aqueous sodium chloride solution (once),
  3. dry with materialdried over magnesium sulfate
  4. concentrationfinally concentrated
  5. distillationThe crude product was purified by distillation

Sources & evidence

ORD record
ord-01fdac9848bc4eada90f42c5875f2bd3
Source dataset
uspto-grants-2000_04
Patent number
US06054413

Reaction notes

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