1-Bromo-3-chloropropane → HCID 10777231, compound

HRID 263462Notes

Reaction equation

HRID 263462 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:13])[CH:7]=[C:8]([CH3:12])[O:9]2)=[CH:4][CH:3]=1.Br[CH2:15][CH2:16][CH2:17][Cl:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(OCC)C>[Cl:18][CH2:17][CH2:16][CH2:15][O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:13])[CH:7]=[C:8]([CH3:12])[O:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 53553097-hydroxy-2-methyl-4H-1-benzopyran-4-one

Product 1

HCID 10777231HCID 10777231, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

3.9 g (20 mmole) of 7-hydroxy-2-methylchromen-4-one, 4.4 ml (40 mmole) of 1-bromo-3-chloropropane and 6.1 g (40 mmole) of anhydrous potassium carbonate in 100 ml of acetone were mixed and refluxed under heating for 16 hours. The mixture was allowed to cool and the insoluble solid was separated by filtration. The filtrate was evaporated to dryness, and the residue obtained was suspended in ethyl ether, filtered, washed with ether and dried at vaccum to yield 4.76 g (85%) of the product, melting point 113°-115° C.

Workup

  1. temperaturerefluxed
  2. temperatureunder heating for 16 hours
  3. temperatureto cool
  4. customthe insoluble solid was separated by filtration
  5. customThe filtrate was evaporated to dryness
  6. customthe residue obtained
  7. filtrationfiltered
  8. washwashed with ether
  9. customdried at vaccum

Sources & evidence

ORD record
ord-7aae930d49a248dfbc137b81416c4dbc
Source dataset
uspto-grants-1997_07
Patent number
US05643927

Reaction notes

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