Acetone → HCID 67241424, compound

HRID 1949565Notes

Reaction equation

HRID 1949565 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([Cl:9])[CH:3]=1.[Li]CCCC.[CH3:15][C:16]([CH3:18])=[O:17]>C1COCC1>[Cl:9][C:4]1[CH:3]=[C:2]([C:16]([OH:17])([CH3:18])[CH3:15])[CH:7]=[CH:6][C:5]=1[CH3:8]

Participants

5

Reactant 3

HCID 180AcetoneHCID 27355544-Bromo-2-chlorotolueneHCID 178418339Butyllithium

Product 1

HCID 67241424HCID 67241424, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 4-bromo-2-chlorotoluene (10 g, 48.7 mmol) in THF was added n-BuLi at −78° C. After the reaction mixture was stirred at −78° C. for 30 minutes, dry acetone was slowly added. The resulting content was maintained at −78° C. for 3 hours and slowly warmed up to RT overnight. The reaction mixture was then partitioned between ethyl acetate and water. The ethyl acetate layer was then washed with brine, dried over Na2SO4, filtered, and the solvent evaporated in vacuo to yield a crude oil. The crude solid was purified via flash chromatography (30% EtOAc in n-hexane) yielded the title compound as an oil (7.2 g, 80%)

Workup

  1. temperatureThe resulting content was maintained at −78° C. for 3 hours
  2. temperatureslowly warmed up to RT overnight
  3. customThe reaction mixture was then partitioned between ethyl acetate and water
  4. washThe ethyl acetate layer was then washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent evaporated in vacuo
  8. customto yield a crude oil
  9. customThe crude solid was purified via flash chromatography (30% EtOAc in n-hexane)

Sources & evidence

ORD record
ord-aa070b0913bd46c1abb130d3070ee83d
Source dataset
uspto-grants-2013_03
Patent number
US08399681B2

Reaction notes

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