Sodium Acetate → 1-Chloro-2-ethyl-3-fluorobenzene

HRID 2046636Notes

Reaction equation

HRID 2046636 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH:9]=[CH2:10].C([O-])(=O)C.[Na+]>C(OCC)(=O)C.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][CH3:10]

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 121749902-Chloro-6-fluorostyrene

Product 1

HCID 20401631-Chloro-2-ethyl-3-fluorobenzeneYield 87.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution (120 mL) of 1-chloro-3-fluoro-2-vinylbenzene (9.45 g) in ethyl acetate were added sodium acetate (4.92 g) and 10% Pd/C (50% water-containing product, 0.95 g), and the mixture was vigorously stirred under a hydrogen atmosphere. The catalyst was filtered off, and the filtrate was concentrated. The residue was partitioned with ethyl acetate-water. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated to give the title compound as a colorless oil (yield: 8.4 g).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was partitioned with ethyl acetate-water
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-24cbfa1e64fa48f5bc9935b95c64e086
Source dataset
uspto-grants-2013_11
Patent number
US08592452B2

Reaction notes

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