2-{2-Chloro-4-fluoro-3-[prop-1-en-1-yl]phenyl}-1,3-dioxolane → 2-Chloro-1-(dimethoxymethyl)-4-fluoro-3-propylbenzene

HRID 2046645Notes

Reaction equation

HRID 2046645 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]=[CH:9][CH3:10])=[C:6]([F:11])[CH:5]=[CH:4][C:3]=1[CH:12]1[O:16][CH2:15][CH2:14][O:13]1>CO.[Pd]>[Cl:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([F:11])[CH:5]=[CH:4][C:3]=1[CH:12]([O:16][CH3:15])[O:13][CH3:14]

Participants

4

Reactant 1

HCID 686033642-{2-Chloro-4-fluoro-3-[prop-1-en-1-yl]phenyl}-1,3-dioxolane

Product 1

HCID 593705302-Chloro-1-(dimethoxymethyl)-4-fluoro-3-propylbenzeneYield 93.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of the obtained 2-{2-chloro-4-fluoro-3-[prop-1-en-1-yl]phenyl}-1,3-dioxolane (1.41 g) in methanol (20 ml) was added finely shredded palladium-fibroin (200 mg), and the mixture was vigorously stirred under a hydrogen atmosphere for 12 hr. The reaction mixture was filtered by suction through a glass filter with a layer of celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate=30:1→3:1) to give the title compound as a colorless oil (yield: 1.34 g).

Workup

  1. filtrationThe reaction mixture was filtered by suction through a glass
  2. filtrationfilter with a layer of celite, and the filtrate
  3. concentrationwas concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate=30:1→3:1)

Sources & evidence

ORD record
ord-f252a7ed8d144bcb8808106449a37cb8
Source dataset
uspto-grants-2013_11
Patent number
US08592452B2

Reaction notes

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