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

HRID 2042615Notes

Reaction equation

HRID 2042615 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-e4c835008b5d4674a9a8d9d80b44a88e
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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