1-Bromo-3-chloropropane → HCID 23286062, compound

HRID 369433Notes

Reaction equation

HRID 369433 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[O:12][C:11]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[C:10]([OH:22])[C:9]2=[O:23])=[O:5])[CH3:2].Br[CH2:25][CH2:26][CH2:27][Cl:28].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:28][CH2:27][CH2:26][CH2:25][O:22][C:10]1[C:9](=[O:23])[C:8]2[C:13](=[CH:14][CH:15]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:7]=2)[O:12][C:11]=1[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 23286075HCID 23286075, compound

Product 1

HCID 23286062HCID 23286062, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

6-Ethoxycarbonyl-3-hydroxyflavone (3.2 mmol), 1-bromo-3-chloropropane (3.2 mmol) and potassium carbonate (3.2 mmol) were dissolved in 20 ml of DMF, followed by stirring at 100° C. for 2 hours. The reaction mixture was concentrated under reduced pressure. Chloroform was added to the residue, and an insoluble mater was removed. The filtrate was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column (petroleum ether:ethyl acetate=2:1), whereby the title compound represented by the following formula was obtained as a colorless oil (yield: 38%). ##STR61##

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionChloroform was added to the residue
  3. customan insoluble mater was removed
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by chromatography on a silica gel column (petroleum ether:ethyl acetate=2:1), whereby the title compound

Sources & evidence

ORD record
ord-b64d4b7b9f3d47ca9d09de24a39e1c37
Source dataset
uspto-grants-2000_10
Patent number
US06136848

Reaction notes

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