Hydrochloric Acid → 3-Chloro-1-(3-chlorophenyl)-1-propanone

HRID 1396305Notes

Reaction equation

HRID 1396305 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([Mg]Br)[CH:5]=[CH:6][CH:7]=1.[Cl:10][CH2:11][CH2:12][C:13](Cl)=[O:14].Cl>C1COCC1.[Cl-].[Zn+2].[Cl-].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:10][CH2:11][CH2:12][C:13]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)=[O:14]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 693643-Chloropropionyl chlorideHCID 178478127HCID 178478127, compound

Product 1

HCID 674703793-Chloro-1-(3-chlorophenyl)-1-propanoneYield 31.3%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of zinc chloride (0.5 M in THF, 20.40 mL, 10.20 mmol) was added a solution of (3-chlorophenyl) magnesium bromide (0.5 M in THF, 20.00 mL, 10 mmol) and the mixture was stirred at ambient temperature for 20 min. Pd(PPh3)4 (578 mg, 0.500 mmol) was added to the above mixture and the reaction was then cooled to 0° C. A solution of 3-chloropropanoyl chloride (1.008 mL, 10.50 mmol) in THF (anhydrous) (10 mL) was added and the reaction was stirred at 0° C. for 2 h. After this time, the mixture was acidified with 3 N HCl and extracted with Et2O (3×). The combined organic layer was washed with saturated aqueous NaHCO3, brine, dried (Na2SO4), filtered and evaporated to an oil which was purified using silica gel chromatography to give the desired product (635 mg, 31%). MS (ESI) m/z: 202.9 (M+H)+.

Workup

  1. temperaturethe reaction was then cooled to 0° C
  2. stirringthe reaction was stirred at 0° C. for 2 h
  3. extractionextracted with Et2O (3×)
  4. washThe combined organic layer was washed with saturated aqueous NaHCO3, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated to an oil which
  8. customwas purified

Sources & evidence

ORD record
ord-2ea0931bd24b4916b175be1c1efde405
Source dataset
uspto-grants-2014_12
Patent number
US08901115B2

Reaction notes

Loading…