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

HRID 1193655Notes

Reaction equation

HRID 1193655 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-1d3796b9bd5546fbbca0c727992f995a
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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