1,2-Dimethoxyethane → (2-chlorobenzyl)(4-chlorophenyl)methanone

HRID 1409539Notes

Reaction equation

HRID 1409539 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5](CBr)=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:19]=[CH:18][C:14](C(Cl)=O)=[CH:13][CH:12]=1.[CH2:20]([CH2:23][O:24]C)OC>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]>[Cl:10][C:11]1[CH:19]=[CH:18][CH:14]=[CH:13][C:12]=1[CH2:20][C:23]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:9][CH:8]=1)=[O:24]

Participants

6

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 85014-Chlorobenzoyl chlorideHCID 693291-(Bromomethyl)-4-chlorobenzene

Product 1

HCID 246599(2-chlorobenzyl)(4-chlorophenyl)methanoneYield 91%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

To dimethoxyethane (100 mL) were added 4-chlorobenzyl bromide (4.1 g), 4-chlorobenzoyl chloride (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 atmosphere. The reaction mixture was filtered and the filtrate was concentrated in vacuo and extracted with ethyl acetate. The organic layer was washed with 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 give (2-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 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-477b9cd8fb05468595b952aab2f86e16
Source dataset
uspto-grants-2014_12
Patent number
US08921380B2

Reaction notes

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