4-Chlorobenzoyl chloride → 1,2-Bis(4-chlorophenyl)ethanone

HRID 1929749Notes

Reaction equation

HRID 1929749 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](Cl)=[O:16])=[CH:13][CH:12]=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Zn].C(COC)OC>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][C:15]([C:14]2[CH:18]=[CH:19][C:11]([Cl:10])=[CH:12][CH:13]=2)=[O:16])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 85014-Chlorobenzoyl chlorideHCID 693291-(Bromomethyl)-4-chlorobenzene

Product 1

HCID 5873181,2-Bis(4-chlorophenyl)ethanoneYield 91%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To dimethoxyethane (100 mL) was added 4-chlorobenzylbromide (4.1 g), 4-chlorobenzoylchloride (2.56 mL), bis(triphenylphosphine)palladium dichloride (702 mg) and zinc powder (2.6 g) and the mixture was stirred for 2 hours under nitrogen gas atmosphere. The reaction mixture was filtered and the filtrate was concentrated in vacuo and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo and the resultant crude product was purified by column chromatography on silica gel (solvent: hexane/ethyl acetate=49/1 to 9/1) to obtain (4-chlorobenzyl) (4-chlorophenyl)methanone (4.85 g, yield: 91%) as a powder.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo
  8. customthe resultant crude product was purified by column chromatography on silica gel (solvent: hexane/ethyl acetate=49/1 to 9/1)

Sources & evidence

ORD record
ord-141bdf3e115e4f1880b6d39bbbd074af
Source dataset
uspto-grants-2012_05
Patent number
US08188097B2

Reaction notes

Loading…