1-Bromo-3-chloropropane → HCID 59651882, compound

HRID 221845Notes

Reaction equation

HRID 221845 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][CH:6]([CH3:16])[C:7]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)=[O:8])[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](=[O:17])[CH2:5][CH:6]([CH3:16])[C:7]([C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:19][CH2:20][CH2:21][Cl:22])=[CH:13][CH:14]=1)=[O:8])[CH3:2]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 596519524-(4-Hydroxyphenyl)-3-methyl-4-oxo-butyric acid ethyl ester

Product 1

HCID 59651882HCID 59651882, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-(4-hydroxyphenyl)-3-methyl-4-oxo-butyric acid ethyl ester (12.5 g, 52.9 mmol), 1-bromo-3-chloropropane (11.3 mL, 114.6 mmol) and K2CO3 (21.9 g, 159 mmol) in acetone (200 mL) was stirred at 60° C. for 15 h. The reaction was cooled to RT and filtered over celite and the filtrate was evaporated at reduced pressure to give a crude residue. The crude residue was partitioned between methylene chloride and saturated aqueous sodium bicarbonate solution and the aqueous layer was extracted twice with methylene chloride. The combined organics was washed with brine, dried (Na2SO4), filtered, and concentrated to provide a crude product. The crude product was purified by ISCO (330 g) chromatography using 15% EtOAc in hexane to produce 4-[4-(3-chloro-propoxy)-phenyl]-3-methyl-4-oxo-butyric acid ethyl ester (9.7 g, 56%), MS m/z 267 (M−45).

Workup

  1. temperatureThe reaction was cooled to RT
  2. filtrationfiltered over celite
  3. customthe filtrate was evaporated at reduced pressure
  4. customto give a crude residue
  5. customThe crude residue was partitioned between methylene chloride and saturated aqueous sodium bicarbonate solution
  6. extractionthe aqueous layer was extracted twice with methylene chloride
  7. washThe combined organics was washed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto provide a crude product
  12. customThe crude product was purified by ISCO (330 g) chromatography

Sources & evidence

ORD record
ord-02ee07e2d3fd4559b01fd97bc0d96b87
Source dataset
uspto-grants-2012_06
Patent number
US08207168B2

Reaction notes

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