1-Bromo-3-chloropropane → HCID 9995573, compound

HRID 1709832Notes

Reaction equation

HRID 1709832 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:16]=[C:15]([OH:17])[CH:14]=[CH:13][C:9]=2[C:10](=[O:12])[CH:11]=1)=[O:5])[CH3:2].Br[CH2:19][CH2:20][CH2:21][Cl:22].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:16]=[C:15]([O:17][CH2:19][CH2:20][CH2:21][Cl:22])[CH:14]=[CH:13][C:9]=2[C:10](=[O:12])[CH:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 5376802ethyl 7-hydroxy-4-oxo-4H-chromen-2-carboxylate

Product 1

HCID 9995573HCID 9995573, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 23.4 g (0.1 mole) of 7-hydroxy-4-oxo-4H-1-benzopyran-2-carboxylic acid ethyl ester, 31.6 g (0.2 mole) of 1-bromo-3-chloropropane and 41.5 g (0.3 mole) of anhydrous potassium carbonate in 500 ml of acetone was heated at reflux for 20 hr. The mixture was cooled and filtered through Celite®. The filtrate was concentrated under reduced pressure to give a solid residue. The solid was triturated with petroleum ether (30°-60° C.), collected by filtration, and recrystallized from 2-propanol to yield 22.5 g (73%) of white solid, m.p. 107°-108° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 hr
  3. temperatureThe mixture was cooled
  4. filtrationfiltered through Celite®
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto give a solid residue
  7. customThe solid was triturated with petroleum ether (30°-60° C.)
  8. filtrationcollected by filtration
  9. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-b41ca857ba4745c3b0378dc15e59771f
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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