Potassium Acetate → 2,6-Dichloro-3-nitrophenylmethyl acetate

HRID 1759206Notes

Reaction equation

HRID 1759206 reaction equation
Br[CH2:2][C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[C:5]([N+:10]([O-:12])=[O:11])[C:4]=1[Cl:13].[C:14]([O-:17])(=[O:16])[CH3:15].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[C:14]([O:17][CH2:2][C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[C:5]([N+:10]([O-:12])=[O:11])[C:4]=1[Cl:13])(=[O:16])[CH3:15]

Participants

5

Reactant 2

HCID 517044Potassium AcetateHCID 110115352,6-Dichloro-3-nitrobenzyl Bromide

Product 1

HCID 155817582,6-Dichloro-3-nitrophenylmethyl acetateYield 50%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6342AcetonitrileSolvent

Procedure

A rapidly stirred solution of the mixture from Step A, 20.6 grams (0.21 mole) of potassium acetate and 3.0 grams of tetrabutylammonium bromide in 250 ml of acetonitrile was heated under reflux for 24 hours. The reaction mixture was cooled and filtered. The filtrate was washed with two portions of an aqueous solution saturated with sodium chloride. The organic layer was slurried with magnesium sulfate, decolorizing carbon, and 500 grams of silica gel. The mixture was filtered and the filtrate concentrated under reduced pressure to give 28.7 grams of 50% 2,6-dichloro-3-nitrophenylmethyl acetate and 50% 2,6-dichloro-3-nitrotoluene. The nmr and the ir spectra were consistent with the proposed structure.

Workup

  1. temperatureunder reflux for 24 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. washThe filtrate was washed with two portions of an aqueous solution saturated with sodium chloride
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-cf1d3f2ddf514ae0a91ca1bf67278eb0
Source dataset
uspto-grants-1982_07
Patent number
US04339457

Reaction notes

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